Abstract
Constrained enantiopure bicyclic β-amino acids derived from the asymmetric Diels–Alder reaction of the (R)-benzyl-4-(3-acryloyloxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)-benzoate and the 1-(benzyloxycarbonylamino)cyclohexadiene provide original templates for the construction of new rigid enantiopure 1,3-amino alcohols.
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References
Ager DJ, Prakash I, Schaad DR (1996) 1, 2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis. Chem Rev 96:835–876
Akkari R, Calmès M, Escale F, Iapichella J, Rolland M, Martinez J (2004) (R)- or (S)-4-(3-hydroxy-4, 4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels–Alder reactions. Tetrahedron Asymmetr 15:2515–2525
Balazs AS, Szakonyi Z, Fülöp F (2007) Synthesis of alicyclic N-substituted 1, 3-aminoalcohols via 1, 3-oxazines. J Heterocyclic Chem 44:403–406
Barluenga J, Viado AL, Aguilar E, Fustero S, Olano B (1993) 1, 3-Amino alcohols from 4-amino-1-azadienes. Diastereo- and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX. J Org Chem 58:5972–5975
Bartoli G, Cimarelli C, Marcantoni E, Palmieri G, Petrini M (1994) Chemo- and diastereoselective reduction of beta-enamino esters: a convenient synthesis of both cis- and trans-γ-amino alcohols and β-amino esters. J Org Chem 59:5328–5335
Binder CM, Bautista A, Zaidlewicz M, Krzemiński MP, Oliver A, Singaram B (2009) Stereoselectivity in the dialkylzinc reaction using (−)-β-pinene derived amino alcohol chiral auxiliaries. J Org Chem 74:2337–2343
Blaser HU (1992) The chiral pool as a source of enantioselective catalysts and auxiliaries. Chem Rev 92:935–952
Calmès M, Didierjean C, Martinez J, Songis O (2005) (R)-(4-(Benzyloxycarbonylphenyl)-3-hydroxy-4, 4-dimethyl-2-pyrrolidinone) acrylate derivative as a chiral dienophile for the synthesis of enantiopure 2-aminocyclohexane carboxylic acids. Tetrahedron Asymmetr 16:2173–2178
Corey EJ, Helal CJ (1998) Reduction of carbonyl compounds with chiral oxazaborolidine catalysts: A new paradigm for enantioselective catalysis and a powerful new synthetic sethod. Angew Chem Int Ed Engl 37:1986–2012
Corey EJ, Bakshi RK, Shibata S (1987) Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications. J Am Chem Soc 109:5551–5553
Delair P, Einhorn C, Einhorn J, Luche JL (1994) Synthesis of beta-amino alcohols derived from l-valine. J Org Chem 59:4680–4682
Deloux L, Screbnik M (1993) Asymmetric boron-catalyzed reactions. Chem Rev 93:763–784
Didier E, Loubinoux B, Ramos Tombo GM, Rihs G (1991) Chemo-enzymatic synthesis of 1, 2- and 1, 3-aminoalcohols and their use in the enantioselective reduction of acetophenone and anti-acetophenone oxime methyl ether with borane. Tetrahedron 47:4941–4958
Fülöp F (2001) The chemistry of 2-aminocycloalkanecarboxylic acids. Chem Rev 101:2181–2204
Fülöp F, Szakonyi Z, Bernath G, Sohar P (1997) Saturated heterocycles: synthesis of 2, 4-dioxo and 4-oxo-2-thioxo derivatives of octahydrocyclopenta[d]pyrimidines. J Heterocyclic Chem 34:1211–1214
Garcia Martinez A, Teso Vilar E, Garcıa Fraile A, de la Moya Cerero S, Martinez Ruiz P, Chicharro Villas P (2002) Bridgehead-norbornane-derived β-amino alcohol catalysts: structural factors influencing the chirality transfer. Tetrahedron Asymmetr 13:1–4
Gyonfalvi S, Szakonyi Z, Fülöp F (2003) Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene. Tetrahedron Asymmetr 14:3965–3972
Hobuss D, Baro A, Laschat S, Frey W (2008) Catalytic enantioselective borane reduction of arylketones with pinene-derived amino alcohols. Tetrahedron 64:1635–1640
Khalil EM, Subasinghe NL, Johnson RL (1996) An efficient and high yield method for the N-tert-butyloxycarbonyl protection of sterically hindered amino acids. Tetrahedron Lett 37:3441–3444
Kiss L, Fülöp F (2009) Selective syntheses of functionalized cyclic β-amino acids via transformation of the ring C-C double bonds. Synlett 9:1302–1314
Kiss L, Forró E, Fülöp F (2009) Synthesis of carbocyclic β-amino acids. In: Hughes AB (ed) Amino acids, peptides and proteins in organic chemistry: origins and synthesis of amino acids, vol 1. Wiley-VCH, Weinheim, pp 367–409
Kitamura M, Suga S, Kawai K, Noyori R (1986) Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes. J Am Chem Soc 108:6071–6072
Kivelä H, Klika KD, Szabo A, Stajer G, Pihlaja K (2003) Structures of saturated 5H-pyrrolo[1,2-a][3,1]benzoxazin-1(2H)-ones prepared from 4-oxopentanoic acid and cyclic amino alcohols. Eur J Org Chem 1879–1886
Kivelä H, Zalan Z, Tahtinen P, Sillanpää R, Fülöp F, Pihlaja K (2005) Synthesis and conformational analysis of saturated 3, 1, 2-benzoxazaphosphine 2-oxides. Eur J Org Chem 9:1189–1200
Kochi T, Tang TP, Ellman JA (2003) Development and application of a new general method for the asymmetric synthesis of syn- and anti-1, 3-amino alcohols. J Am Chem Soc 125:11276–11282
Kossenjans M, Martens J (1998) Synthesis of C 2-symmetrical bis-β-amino alcohols from (R)-cysteine and their application in enantioselective catalysis. Tetrahedron Asymmetr 9:1409–1417
Kossenjans M, Martens J (1999) Highly stereoselective synthesis of 1, 3-aminoalcohols via Mannich reactions. Tetrahedron Asymmetr 10:3409–3416
Krzemiński MP, Wojtczak A (2005) Chiral terpene auxiliaries Part 1: Highly enantioselective reduction of ketones with borane catalyzed by an oxazaborolidine derived from (-)-β-pinene. Tetrahedron Lett 46:8299–8302
Krzemiński MP, Zaidlewicz M (2003) Asymmetric reduction of ketoxime derivatives and N-alkylketimines with borane-oxazaborolidine adducts. Tetrahedron Asymmetr 14:1463–1466
Laczkowski K, Kmieciak A, Kozakiewicz A (2009) Stereoselective synthesis of new monoterpene β-amino alcohols. Tetrahedron Asymmetr 20:1487–1492
Lait SM, Rankic DA, Keay BA (2007) 1, 3-Aminoalcohols and their derivatives in asymmetric organic synthesis. Chem Rev 107:767–796
Li X, Yeung CH, Chan ASC, Yang TK (1999) New 1, 3-amino alcohols derived from ketopinic acid and their application in catalytic enantioselective reduction of prochiral ketones. Tetrahedron Asymmetr 10:759–763
Masui M, Shiori T (1998) Stereoselective synthesis of 1, 2-amino alcohols by asymmetric borane reduction of α-oxoketoxime ethers. Tetrahedron Lett 39:5195–5198
McGeary RP (1998) Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride. Tetrahedron Lett 39:3319–3322
Murai T, Sano H, Kawai H, Aso H, Shibahara F (2005) N-Thioacyl-1, 3-amino alcohols: synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5, 6-dihydro-4H–1, 3-oxazines and 1, 3-amino alcohols. J Org Chem 70:8148–8153
Oliveira L, Costa V (2004) An efficient synthesis of enantiopure (+)- and (−)-syn-1, 3-amino alcohols with the norbornane framework and their application in the asymmetric addition of ZnEt2 to benzaldehyde. Tetrahedron Asymmetr 15:2583–2590
Park K-H, Kurth MJ (2002) Cyclic amino acid derivatives. Tetrahedron 58:8629–8659
Raghavan S, Rajender A, Joseph SC, Rasheed MA, Kumar KR (2004) Regio- and stereoselective synthesis of 1, 3-aminoalcohol derivatives from allylamine derivatives via internal sulfinyl group participation. Tetrahedron Asymmetr 15:365–379
Reetz MT, Drewes MW, Schmitz A (1987) Stereoselective synthesis of β-amino alcohols from optically active α-amino acids. Angew Chem Int Ed Engl 26:1141–1143
Scarpi D, Occhiato EG, Guarna A (2009) Asymmetric addition of diethylzinc to aldehyde catalyzed by a camphor-derived β-amino alcohol. Tetrahedron Asymmetr 20:340–350
Songis O, Géant PY, Sautrey G, Martinez J, Calmès M (2008) Asymmetric Diels-Alder reaction of nonracemic acrylate bound to Rink resin with some aminodienes: a comparison of these reactions to their solution state analogues. Eur J Org Chem 308–318
Songis O, Didierjean C, Martinez J, Calmès M (2007) Asymmetric Diels-Alder cycloaddition of 1-aminocyclohexadiene to chiral acrylate: Synthesis of enantiopure bridgehead aminobicyclo[2.2.2]octane-2-carboxylic acid derivatives. Eur J Org Chem 3166–3172
Songis O, Didierjean C, Martinez J, Calmès M (2008b) The iodolactone approach to enantiopure oxiranes of constrained chiral cyclic β-amino acids. Tetrahedron Asymmetr 19:2135–2139
Szakonyi Z, Balazs A, Martinek TA, Fülöp F (2006) Enantioselective addition of ZnEt2 to aldehyde catalyzed by γ-amino alcohols derived from (+)- and (−)-α-pinène. Tetrahedron Asymmetr 17:199–204
Wu ZL, Wu HL, Wu PY, Uang BJ (2009) N-Substituent effects on the diethylzinc addition to benzaldehyde catalyzed by bicyclic 1, 4-aminoalcohols. Tetrahedron Asymmetr 20:1556–1560
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The authors gratefully acknowledge the CNRS and the MESR for their financial support.
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André, C., Calmès, M., Escale, F. et al. New 1,3-amino alcohols derived from enantiopure bridgehead β-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acids. Amino Acids 43, 415–421 (2012). https://doi.org/10.1007/s00726-011-1097-6
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DOI: https://doi.org/10.1007/s00726-011-1097-6