Abstract
Ring-forming reactions are an essential part of synthetic chemistry and allow access to a range of useful natural products and biologically important molecules. The applications of organocatalysis to the synthesis of functionalised, enantiopure structures really begins where organocatalysis itself begins; with the Hajos-Parrish reaction in the 1970s for the synthesis of steroids using proline. This chapter then will review the uses of organocatalysts in cyclization methodology – from the initial Hajos-Parrish discovery to current advances in the field.
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References
(a) Baldwin JE (1976) J Chem Soc Chem Comm 734; (b) Baldwin JE, Cutting J, Dupont W, Kruse L, Silberman L, Thomas RC (1976) J Chem Soc Chem Comm 736; (c) Baldwin JE, Kruse LI (1977) J Chem Soc Chem Comm 233; (d) Baldwin JE, Lusch MJ (1982) Tetrahedron 38:2939
Zampella A, D’Auria MV, Minale L, Debitus C, Roussakis C (1996) J Am Chem Soc 118:11085
Papageorgiou CD, Ley SV, Gaunt MJ (2003) Angew Chem Int Ed 42:828
Bremeyer N, Smith SC, Ley SV, Gaunt MJ (2004) Angew Chem Int Ed 43:2681
Papageorgiou CD, de Dios MA Cubillo, Ley SV, Gaunt MJ (2004) Angew Chem Int Ed 43:4641
Kunz RK, MacMillan DWC (2005) J Am Chem Soc 127:3240
Xie H, Zu L, Li H, Wang J, Wang W (2007) J Am Chem Soc 129:10886
Xuan Y-N, Nie S-Z, Dong L-T, Zhang J-M, Yan M (2009) Org Lett 11:1583
(a) Wynberg H, Staring EGJ (1982) J Am Chem Soc 104:166; (b) Wynberg H, Staring EGJ (1985) J Org Chem 50:1977
Cortez GS, Tennyson RL, Romo D (2001) J Am Chem Soc 123:7945
Hodous BL, Fu GC (2002) J Am Chem Soc 124:1578
(a) Hajos ZG, Parrish DR (1971) German Patent DE 2102623; (b) Hajos ZG, Parrish DR (1974) J Org Chem 39:1615
Eder U, Sauer G, Wiechert R (1971) Angew Chem Int Ed 10:496
Clemente FR, Houk KN (2004) Angew Chem Int Ed 43:5766
Shigehisa H, Mizutani T, Tosaki S-y, Ohshima T, Shibasaki M (2005) Tetrahedron 61:5057
List B, Lerner RA, Barbas CF (2000) J Am Chem Soc 122:2395
Pidathala C, Hoang L, Vignola N (2003) Angew Chem Int Ed 42:2785
(a) Cobb AJA, Shaw DM, Ley SV (2004) Synlett 558; (b) Hartikka A, Arvidsson PI (2004) Tetrahedron: Asymm 15:1831; (c) Torii H, Nakadai M, Ishihara K, Saito S, Yamamoto H (2004) Angew Chem Int Ed 43:1983
Enders D, Niemeier O, Leo S (2006) Synlett 3399
Itagaki N, Kimura M, Sugahara T, Iwabuchi Y (2005) Org Lett 7:4185
Frisch K, Landa A, Saaby S, Jorgensen KA (2005) Angew Chem Int Ed 44:6058
(a) Hechavarria MT, List B (2004) Angew Chem Int Ed 43:3958; For a related study see (b) Kikuchi M, Inagaki T, Nishiyama H (2007) Synlett 1075
Mangion IK, MacMillan DWC (2005) J Am Chem Soc 127:3696
(a) Hayashi Y, Gotoh H, Tamura T, Yamaguchi H, Masui R, Shoji M (2005) J Am Chem Soc 127:16028
Fustero S, Jiménez D, Moscardó J, Catalán S, del Pozo C (2007) Org Lett 9:5283
A related protocol has been described by Carlson EC, Rathbone LK, Collett ND, Carter RG (2008) J Org Chem 73:5155
Vignola N, List B (2004) J Am Chem Soc 126:450
Fu A, List B, Thiel W (2006) J Org Chem 71:320
Bihelovic F, Matovic R, Vulovic B, Saicic RN (2007) Org Lett 9:5063
For the intermolecular version of this process, see Ibrahem I, Córdova A (2006) Angew Chem Int Ed 45:1952
For a useful review in combining transition metal catalysis and organocatalysis, see Shao Z, Zhang, H (2009) Chem Soc Rev 38:2745
Beeson TD, Mastracchio A, Hong J-B, Ashton K, MacMillan DW C (2007) Science 316:582
Conrad JC, Kong J, Laforteza BN, MacMillan DWC (2009) J Am Chem Soc 131:11640
For a contrasting report see Nicolaou KC, Reingruber R, Sarlah D, Bräse S (2009) J Am Chem Soc 131:2086
For a useful review see (a) Akiyama T (2007) Chem Rev 107:5744 which makes up a special issue on organocatalysis; (b) Connon SJ (2008) Chem Commun 2499
Taylor MS, Jacobsen EN (2004) J Am Chem Soc 126:10558
Raheem IT, Thiara PS, Peterson EA, Jacobsen EN (2007) J Am Chem Soc 129:13404
Kam T-S, Sim K-M (1998) Phytochemistry 47:145
(a) Ciamician G, Plancher G (1896) Chem Ber 29:2475; (b) Jackson AH, Smith P (1968) Tetrahedron 24:2227
Seayad J, Seayad AM, List B (2006) J Am Chem Soc 128:1086
Wanner MJ, van der Haas RNS, de Cuba KR, van Maarseveen JH, Hiemstra H (2007) Angew Chem Int Ed 46:7485
Sewgobind NV, Wanner MJ, Ingemann S, de Gelder R, van Maarseveen JH, Hiemstra H (2008) J Org Chem 73:6405
Muratore ME, Holloway CA, Pilling AW, Storer RI, Trevitt G, Dixon DJ (2009) J Am Chem Soc 131:10796
Nodes WJ, Nutt DR, Chippindale AM, Cobb AJA (2009) J Am Chem Soc 131:16016
(a) Gellman SH (1998) Acc Chem Res 31:173; (b) Horne WS, Gellman SH (2008) Acc Chem Res 41:1399
Chebib M, Johnston GAR (2000) J Med Chem 43:1427
Marion N, Díez-González S, Nolan SP (2007) Angew Chem Int Ed 46:2988
Enders D, Breuer K, Runsink J, Teles JJ (1996) Helv Chim Acta 79:1899
(a) Kerr MS, de Alaniz JR, Rovis T (2002) J Am Chem Soc 124:10298; (b) de Alaniz JR, Kerr MS, Moore JL, Rovis T (2008) J Org Chem 73:2033; (c) de Alaniz JR, Rovis T (2009) Synlett 1189
Moore JL, Kerr MS, Rovis T (2006) Tetrahedron 62:11477
Kerr MS, Rovis T (2004) J Am Chem Soc 126:8876
(a) Hashimoto T, Maruoka K (2007) Chem Rev 107:5656; (b) Ooi T, Maruoka K (2007) Angew Chem Int Ed 46:4222; (c) Jew S-S, Park, H-G (2009) Chem Comm 7090
Bandini M, Eichholzer A, Monari M, Piccinelli F, Umani-Ronchi A (2007) Eur J Org Chem 2007:2917
Bui T, Barbas CF (2000) Tetrahedron Lett 41:6951
McGarraugh PG, Brenner SE (2009) Org Lett 11:5654
Sun F-G, Huang X-L, Ye S (2009) J Org Chem 75:273
Yang JW, Fonseca MTH, List B (2005) J Am Chem Soc 127:15036
Enders D, Hüttl MRM, Grondal C, Raabe G (2006) Nature 441:861
Wang Y, Han R-G, Zhao Y-L, Yang S, Xu P-F, Dixon DJ (2009) Angew Chem Int Ed 48:9834
Córdova A, Notz W, Barbas CF (2001) J Org Chem 67:301
Chowdari NS, Ramachary DB, Córdova A, Barbas CF (2002) Tetrahedron Lett 43:9471
Yamamoto Y, Momiyama N, Yamamoto H (2004) J Am Chem Soc 126:5962
Austin JF, Kim S-G, Sinz CJ, Xiao W-J, MacMillan DWC (2004) Proc Nat Acad Sci USA 101:5482
Jiang J, Yu J, Sun X-X, Rao Q-Q, Gong L-Z (2008) Angew Chem Int Ed 47:2458
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Cobb, A.J.A. (2011). General Aspects of Organocatalytic Cyclizations. In: Mahrwald, R. (eds) Enantioselective Organocatalyzed Reactions II. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3867-8_1
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