Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst

被引：477

作者：

Corey, EJ ^{[1
]}

Grogan, MJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 01期

关键词：

D O I：

10.1021/ol990623l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel catalytic enantioselective Strecker synthesis of chiral a amino nitriles and a-amino acids is described and analyzed with regard to the possible mechanistic basis for stereoselectivity. Key features of the enantioselective process include (1) the use of the chiral bicyclic guanidine 1 as catalyst and (2) the use of the N-benzhydryl substituent on the imine substrate.

引用

页码：157 / 160

页数：4

共 10 条

[1] ENANTIOSPECIFIC SYNTHESIS OF A RIGID, C-2 SYMMETRIC, CHIRAL GUANIDINE BY A NEW AND DIRECT METHOD
COREY, EJ
OHTANI, M
[J]. TETRAHEDRON LETTERS, 1989, 30 (39) : 5227 - 5230
[2] A critical analysis of the mechanistic basis of enantioselectivity in the bis-cinchona alkaloid catalyzed dihydroxylation of olefins
Corey, EJ
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) : 11038 - 11053
[3] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
Corey, EJ
Xu, F
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415
[4] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
DUTHALER, RO
[J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
[5] Ishitani H, 1998, ANGEW CHEM INT EDIT, V37, P3186, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3186::AID-ANIE3186>3.0.CO
[6] 2-E
[7] RETRACTED: Asymmetric catalysis of the Strecker amino acid synthesis by a cyclic dipeptide (Retracted article. See JUN, 2023)
Iyer, MS
Gigstad, KM
Namdev, ND
Lipton, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (20) : 4910 - 4911
[8] Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries
Sigman, MS
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (19) : 4901 - 4902
[9] Enantioselective addition of hydrogen cyanide to imines catalyzed by a chiral (salen)Al(III) complex
Sigman, MS
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) : 5315 - 5316
[10] Strecker A., 1850, Justus Liebigs Ann. Chem, V75, P27, DOI [DOI 10.1002/JLAC.18500750103, 10.1002/jlac.18500750103]

← 1 →