Abstract
Reactions of allylic boranes with aldehydes have proved to be among the most efficient means of building a stereocontrolled set of several adjacent chiral centers. Boron enolates follow a similar mechanistic path and have also provided significant advances in asymmetric synthesis. The chemistry described in this chapter has been the key to a considerable number of major natural products syntheses, especially of macrolide or ionophore antibiotics.
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References
Mikhailov BM, Bubnov YuN (1964) Izv. Akad. Nauk SSSR, Ser. Khim. 1874
Mikhailov BM, Pozdnev VF (1967) Izv. Akad. Nauk SSSR, Ser. Khim. 1477
Hoffmann RW, Zeiss HJ (1979) Angew. Chem. 91:329; Angew. Chem. Int. Ed. 18:306
Fenzl W, Köster R (1975) Justus Liebigs Ann. Chem. 1322
Fenzl W, Köster R, Zimmermann HJ (1975) Justus Liebigs Ann. Chem. 2201
Masamune S, Mori S, Van Horn D, Brooks DW (1979) Tetrahedron Lett. 1665
Hirama M, Masamune S (1979) Tetrahedron Lett. 2225
Van Horn DE, Masamune S (1979) Tetrahedron Lett. 2229
Hirama M, Garvey DS, Lu LDL, Masamune S (1979) Tetrahedron Lett. 3937
Evans DA, Vogel E, Nelson JV (1979) J. Am. Chem. Soc. 101:6120
Yamamoto Y, Asao N (1993) Chem. Rev. 93:2207
Matteson DS, Campbell JD (1990) Heteroatom Chemistry 1:109
Hoffmann RW, Herold T (1981) Chem. Ber. 114:375
Schlosser M, Rauchschwalbe G (1978) J. Am. Chem. Soc. 100:3258
Schlosser M, Stähle M (1980) Angew. Chem. 92:497; Angew. Chem. Int. Ed. 19:487
Hoffmann RW, Zeiss HJ (1981) J. Org. Chem. 46:1309
Hoffmann RW, Kemper B (1981) Tetrahedron Lett. 22:5263
Hoffmann RW, Kemper B (1982) Tetrahedron Lett. 23:845
Hoffmann RW, Kemper B, Metternich R, Lehmeier T (1985) Justus Liebigs Ann. Chem. 2246
Roush WR, Ando K, Powers DB, Halterman RL, Palkowitz AD (1988) Tetrahedron Lett. 29:5579
Roush WR, Ando K, Powers DB, Palkowitz AD, Halterman RL (1990) J. Am. Chem. Soc. 112:6339
Andersen MW, Hildebrandt B, Köster G, Hoffmann RW (1989) Chem. Ber. 122:1777
Stürmer R (1990) Angew. Chem. 102:62; Angew. Chem. Int. Ed. 29:59
Brown HC, De Lue NR, Yamamoto Y, Maruyama K, Kasahara T, Murahashi S, Sonoda A (1977) J. Org. Chem. 42:4088
Wuts PGM, Bigelow SS (1988) J. Org. Chem. 53:5023
Hoffmann RW, Ditrich K, Köster G, Stürmer R (1989) Chem. Ber. 122:1783
Sadhu KM, Matteson DS (1985) Organometallics 4:1687
Hoffmann RW, Niel G (1991) Justus Liebigs Ann. Chem. 1195
Knöchel P (1990) J. Am. Chem. Soc. 112:7431
Watanabe T, Miyaura N, Suzuki A (1993) J. Organomet. Chem. 444:C1
Hoffmann RW, Sander T, Hense A (1993) Justus Liebigs Ann. Chem. 771
Satoh M, Nomoto Y, Miyaura N, Suzuki A (1989) Tetrahedron Lett. 30:3789
Hoffmann RW (1982) Angew. Chem. 94:569; Angew. Chem. Int. Ed. 21:555
Li Y, Houk KN (1989) J. Am. Chem. Soc. 111:1236
Metternich R, Hoffmann RW (1984) Tetrahedron Lett. 25:4095
Hoffmann RW, Metternich R (1985) Justus Liebigs Ann. Chem. 2390
Hoffmann RW, Kemper B (1984) Tetrahedron 40:2219
Tsai JS, Matteson DS (1981) Tetrahedron Lett. 22:2751
Hoffmann RW, Eichler G, Endesfelder A (1983) Justus Liebigs Ann. Chem. 2000
Hoffmann RW, Endesfelder A (1987) Justus Liebigs Ann. Chem. 215
Hoffmann RW, Endesfelder A (1986) Justus Liebigs Ann. Chem. 1823
Wuts PGM, Jung YW (1986) Tetrahedron Lett. 27:2079
Hoffmann RW, Sander T (1990) Chem. Ber. 123:145
Wang Z, Meng XJ, Kabalka GW (1991) Tetrahedron Lett. 32:1945
Wang Z, Meng XJ, Kabalka GW (1991) Tetrahedron Lett. 32:4619
Wang Z, Meng XJ, Kabalka GW (1991) Tetrahedron Lett. 32:5677
Hoffmann RW, Sander T (1993) Justus Liebigs Ann. Chem. 1185
Hoffmann RW, Sander T (1993) Justus Liebigs Ann. Chem. 1193
Herold T, Schrott U, Hoffmann RW, Schnelle G, Ladner W, Steinbach K (1981) Chem. Ber. 114:359
Roush WR, Walts AE, Hoong LK (1985) J. Am. Chem. Soc. 107:8186
Roush WR, Hoong LK, Palmer MAJ, Park JC (1990) J. Org. Chem. 55:4109
Roush WR, Halterman RL (1986) J. Am. Chem. Soc. 108:294
Roush WR, Park JC (1990) J. Org. Chem. 55:1143
Roush WR, Ratz AM, Jablonski JA (1992) J. Org. Chem. 57:2047
Roush WR, Banfi L (1988) J. Am. Chem. Soc. 110:3979
Roush WR, Banfi L, Park JC, Hoong LK (1989) Tetrahedron Lett. 30:6457
Corey EJ, Imwinkelried R, Pikul S, Xiang YB (1989) J. Am. Chem. Soc. 111:5493
Corey EJ, Yu CM, Kim SS (1989) J. Am. Chem. Soc. 111:5495
Corey EJ, Kim SS (1990) Tetrahedron Lett. 31:3715
Hoffmann RW, Metternich R, Lanz JW (1987) Justus Liebigs Ann. Chem. 881
Hoffmann RW, Brinkmann H, Frenking G (1990) Chem. Ber. 123:2387
Brinkmann H, Hoffmann RW (1990) Chem. Ber. 123:2395
Hoffmann RW, Weidmann U (1985) Chem. Ber. 118:3966
Hoffmann RW, Zeiss HJ, Ladner W, Tabche S (1982) Chem. Ber. 115:2357
Hoffmann RW, Endesfelder A, Zeiss HJ (1983) Carbohydrate Research 123:320
Roush WR, Hoong LK, Palmer MAJ, Straub JA, Palkowitz AD (1990) J. Org. Chem. 55:4117
Masamune S, Choy W., Petersen JS, Sita LR (1985) Angew. Chem. Int. Ed. 24:1.
Roush WR, Palkowitz AD, Palmer MAJ (1987) J. Org. Chem. 52:316
Roush WR, Palkowitz AD, Ando K (1990) J. Am. Chem. Soc. 112:6348
Roush WR (1991) J. Org. Chem. 56:4151
Hoffmann RW, Landmann B (1986) Chem. Ber. 119:1039
Hoffmann RW, Landmann B (1986) Chem. Ber. 119:2013
Stürmer R, Hoffmann RW (1990) Synlett 759
Hoffmann RW, Dresely S (1988) Synthesis 103
Hoffmann RW, Dresely S, Lanz JW (1988) Chem. Ber. 121:1501
Hoffmann RW, Dresely S, Hildebrandt B (1988) Chem. Ber. 121:2225
Hoffmann RW, Giesen V, Fuest M (1993) Justus Liebigs Ann. Chem. 629
Hoffmann RW, Dresely S (1989) Chem. Ber. 122:903
Hoffmann RW, Wolff JJ (1991) Chem. Ber. 124:563
Hoffmann RW, Schlapbach A (1990) Justus Liebigs Ann. Chem. 1243
Hoffmann RW, Schlapbach A (1991) Justus Liebigs Ann. Chem. 1203
Hoffmann RW, Ladner W (1979) Tetrahedron Lett. 4653
Hoffmann RW, Ladner W, Steinbach K, Massa W, Schmidt R, Snatzke G (1981) Chem. Ber. 114:2786
Hoffmann RW, Helbig W (1981) Chem. Ber. 114:2802
Hoffmann RW, Ladner W, Ditrich K (1989) Justus Liebigs Ann. Chem. 883
Ditrich K, Bube T, Stürmer R, Hoffmann RW (1986) Angew. Chem. 98:1016; Angew. Chem. Int. Ed. 25:1028
Hoffmann RW, Ditrich K (1990) Justus Liebigs Ann. Chem. 23
Andersen MW, Hildebrandt B, Dahmann G, Hoffmann RW (1991) Chem. Ber. 124:2127
Roush WR, Palkowitz AD (1987) J. Am. Chem. Soc. 109:953
Roush WR, Palkowitz AD (1989) J. Org. Chem. 54:3009
Roush WR, Kageyama M (1985) Tetrahedron Lett. 26:4327
Roush WR, Brown BB, Drozda SE (1988) Tetrahedron Lett. 29:3541
Roush WR, Coe JW (1987) Tetrahedron Lett. 28:931
Coe JW, Roush WR (1989) J. Org. Chem. 54:915
Danishefsky SJ, Armistead DM, Wincott FE, Seinick HG, Hungate R (1987) J. Am. Chem. Soc. 109:8117
Roush WR, Straub JA (1986) Tetrahedron Lett. 27:3349
Roush WR, Straub JA, Van Niewenhze MS (1991) J. Org. Chem. 56:1636
Corey EJ, Huang HC (1989) Tetrahedron Lett. 30:5235
Ikeda N, Arai I, Yamamoto H (1986) J. Am. Chem. Soc. 108:483
Haruta R, Ishiguro M, Ikeda N, Yamamoto H (1982) J. Am. Chem. Soc. 104:7667
Corey EJ, Yu CM, Lee DH (1990) J. Am. Chem. Soc. 112:878
Corey EJ, Jones GB (1991) Tetrahedron Lett. 32:5713
Midland MM, Preston SB (1980) J. Org. Chem. 45:747
Midland MM, Preston SB (1982) J. Am. Chem. Soc. 104:2330
Brown HC, Jadhav PK (1983) J. Am. Chem. Soc. 105:2092
Brown HC, Jadhav PK (1984) J. Org. Chem. 49:4089
Brown HC, Randad RS, Bhat KS, Zaidlewicz M, Racherla US (1990) J. Am. Chem. Soc. 112:2389
Brown HC, Racherla US, Pellechia PJ (1990) J. Org. Chem. 55:1868
Bubnov YuN, Lavrinovich LI, Zykov AYu, Ignatenko AV (1992) Mendeleev Commun. 86
Brown HC, Racherla US, Liao Y, Khanna VV (1992) J. Org. Chem. 57:6608
Racherla US, Liao Y, Brown HC (1992) J. Org. Chem. 57:6614
Brown HC, Randad RS (1990) Tetrahedron 46:4463
Bubnov YuN, Etinger MYu (1985) Tetrahedron Lett. 26:2797
Brown HC, Jadhav PK (1984) Tetrahedron Lett. 25:1215
Brown HC, Bhat KS (1986) J. Am. Chem. Soc. 108:293
Brown HC, Bhat KS (1986) J. Am. Chem. Soc. 108:5919
Brown HC, Randad RS (1990) Tetrahedron 46:4457
Fujita K, Schlosser M (1982) Helv. Chim. Acta 65:1258
Barrett AGM, Lebold SA (1990) J. Org. Chem. 55:5818
Barrett AGM, Lebold SA (1991) J. Org. Chem. 56:4875
Brown HC, Bhat KS, Randad RS (1987) J. Org. Chem. 52:319
Brown HC, Bhat KS, Randad RS (1987) J. Org. Chem. 52:3701
Brown HC, Bhat KS, Randad RS (1989) J. Org. Chem. 54:1570
Brown HC, Bhat KS, Jadhav PK (1991) J. Chem. Soc. Perkin 1 2633
Barrett AGM, Malecha JW (1991) J. Org. Chem. 56:5243
Garcia J, Kim BM, Masamune S (1987) J. Org. Chem. 52:4831
Short RP, Masamune S (1989) J. Am. Chem. Soc. 111:1892
Evans DA, Taber TR (1980) Tetrahedron Lett. 21:4675
Choy W, Ma P, Masamune S (1981) Tetrahedron Lett. 22:3555
Masamune S, Choy W, Kerdesky FAJ, Imperiali B (1981) J. Am. Chem. Soc. 103:1566
Masamune S, Hirama M, Mori S, Ali SA, Garvey DS (1981) J. Am. Chem. Soc. 103:1568
Masamune S (1981) “Organic Synthesis Today and Tomorrow”, Trost BM, Hutchinson CR, eds, Pergamon Press, Oxford, p. 197
Kaiho T, Masamune S, Toyoda T (1982) J. Org. Chem. 47:1612
Masamune S, Lu LDL, Jackson WP, Kaiho T, Toyoda T (1982) J. Am. Chem. Soc. 104:5523
Masamune S, Imperiali B, Garvey DS (1982) J. Am. Chem. Soc. 104:5528
Masamune S, Kaiho T, Garvey DS (1982) J. Am. Chem. Soc. 104:5521
Boschelli D, Ellingboe JW, Masamune S (1984) Tetrahedron Lett. 25:3395
Masamune S (1988) Annals of the New York Academy of Sciences 544:168
Masamune S, Choy W (1982) Aldrichimica Acta 15 No. 3:47
Masamune S, McCarthy PA (1984) “Macrolide Antibiotics”, Omura S, ed, Academic Press, New York, P. 127
Masamune S (1984) Heterocycles 21:107
Evans DA, Bartroli J, Shih TL (1981) J. Am. Chem. Soc. 103:2127
Evans DA, Nelson JV, Vogel E, Taber TR (1981) J. Am. Chem. Soc. 103:3099
Masamune S, Sato T, Kim BM, Wollmann TA (1986) J. Am. Chem. Soc. 108:8279
Masamune S (1988) Pure Appl. Chem. 60:1587
Kageyama M, Tamura T, Nantz MH, Roberts JC, Somfai P, Whritenour DC, Masamune S (1990) J. Am. Chem. Soc. 112:7408
Duplantier AJ, Masamune S (1990) J. Am. Chem. Soc. 112:7079
Masamune S (1987) “Stereochemistry of Organic and Bioorganic Transformations”, Bartmann W, Sharpless KB, eds, VCH Publishers, Weinheim, Germany, p. 49
Short RP, Masamune S (1987) Tetrahedron Lett. 28:2841
Duplantier AJ, Nantz MH, Roberts JC, Short RP, Somfai P, Masamune S (1989) Tetrahedron Lett. 30:7357
Corey EJ, Kim SS (1990) J. Am. Chem. Soc. 112:4976
Corey EJ, Lee DH (1993) Tetrahedron Lett. 34:1737
Corey EJ, Choi S (1991) Tetrahedron Lett. 32:2857
Corey EJ, Lee DH, Choi S (1992) Tetrahedron Lett. 33:6735
Corey EJ, Decicco CP, Newbold RC. (1991) Tetrahedron Lett. 32:5287
Corey EJ, Lee DH (1991) J. Am. Chem. Soc. 113:4026
Corey EJ, Cywin CL, Roper TD (1992) Tetrahedron Lett. 33:6907
Parmee ER, Tempkin O, Masamune S, Abiko A (1991) J. Am. Chem. Soc. 113:9365
Furata K, Marayama T, Yamamoto H (1991) J. Am. Chem. Soc. 113:1041
Furata K, Marayama T, Yamamoto H (1991) Synlett 439
Furata K, Mouri M, Yamamoto H (1991) Synlett 561
Ishihara K, Mouri M, Bao Q, Marayama T, Furata K, Yamamoto H (1993) J. Am. Chem. Soc. 115:11490
Marshall JA, Tang Y (1992) Synlett 653
Brown HC, Dhar RK, Bakshi RK, Pandiarajan PK, Singaram B (1989) J. Am. Chem. Soc. 111:3441
Brown HC, Dhar RK, Ganesan K, Singaram B (1992) J. Org. Chem. 57:499
Brown HC, Dhar RK, Ganesan K, Singaram B (1992) J. Org. Chem. 57:2716
Brown HC, Ganesan K, Dhar RK (1993) J. Org. Chem. 58:147
Brown HC, Ganesan K, Dhar RK (1992) J. Org. Chem. 57:3767
Brown HC, Ganesan K (1992) Tetrahedron Lett. 33:3421
Evans DA, Fu GC (1990) J. Org. Chem. 55:5678
Curtis ADM, Whiting A (1991) Tetrahedron Lett. 32:1507
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Matteson, D.S. (1995). Allylboron and Boron Enolate Chemistry. In: Stereodirected Synthesis with Organoboranes. Reactivity and Structure Concepts in Organic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-79709-5_7
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