Enantioselective synthesis of α,α-disubstituted-α-amino acids by a sequential nucleophilic addition to nitriles

被引：24

作者：

Charette, AB ^{[1
]}

Mellon, C ^{[1
]}

机构：

[1] Univ Montreal, Dept Chim, Montreal, PQ H3C 3J7, Canada

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00503-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sequential addition of two different nucleophiles to a tartaric acid-derived nitrile produced carbinamines. The adducts from chelation-controlled addition which are obtained in high diastereoselectivities and yields, were easily converted to alpha,alpha-disubstituted-alpha-amino acids. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10525 / 10535

页数：11

共 41 条

[21] AMINO-ALCOHOLS .1. A METHOD FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 1,2-AMINOALCOHOLS WITH ERYTHRO-CONFIGURATION
NOE, CR
KNOLLMULLER, M
GOSTL, G
GARTNER, P
[J]. MONATSHEFTE FUR CHEMIE, 1991, 122 (04): : 283 - 290
[22] L-PHENYLALANINE CYCLOHEXYLAMIDE - A SIMPLE AND CONVENIENT AUXILIARY FOR THE SYNTHESIS OF OPTICALLY PURE ALPHA,ALPHA-DISUBSTITUTED (R)-AMINO AND (S)-AMINO ACIDS
OBRECHT, D
BOHDAL, U
BROGER, C
BUR, D
LEHMANN, C
RUFFIEUX, R
SCHONHOLZER, P
SPIEGLER, C
MULLER, K
[J]. HELVETICA CHIMICA ACTA, 1995, 78 (03) : 563 - 580
[23] ASYMMETRIC-SYNTHESIS WITH CHIRAL BETA-LACTAMS - HIGHLY STEREOSELECTIVE ALKYLATION AND ALDOL REACTION OF A CHIRAL 3-AMINO-4-STYRYL-BETA-LACTAM
OJIMA, I
PEI, YZ
[J]. TETRAHEDRON LETTERS, 1990, 31 (07) : 977 - 980
[24] ASYMMETRIC ALKYLATIONS OF A PHENYLALANYLGLYCINATE EQUIVALENT - NOVEL ROUTE TO DIPEPTIDES BEARING ALPHA-ALKYL-ALPHA-AMINO ACID RESIDUES
OJIMA, I
KOMATA, T
QIU, XG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (02) : 770 - 774
[25] NEW APPROACHES TO THE ASYMMETRIC-SYNTHESIS OF NON-PROTEINOGENIC ALPHA-AMINO-ACIDS AND DIPEPTIDES THROUGH CHIRAL BETA-LACTAM INTERMEDIATES
OJIMA, I
CHEN, HJC
QIU, XG
[J]. TETRAHEDRON, 1988, 44 (17) : 5307 - 5318
[26] THE LONGEST, REGULAR POLYPEPTIDE 3(10) HELIX AT ATOMIC RESOLUTION
PAVONE, V
DIBLASIO, B
SANTINI, A
BENEDETTI, E
PEDONE, C
TONIOLO, C
CRISMA, M
[J]. JOURNAL OF MOLECULAR BIOLOGY, 1990, 214 (03) : 633 - 635
[27] SCHOLLKOPF U, 1986, LIEBIGS ANN CHEM, P2150
[28] SCHOLLKOPF U, 1981, LIEBIGS ANN CHEM, P439
[29] SEEBACH D, 1991, LIEBIGS ANN CHEM, P669
[30] STEREOSELECTIVE ALKYLATION AT C(ALPHA) OF SERINE, GLYCERIC ACID, THREONINE, AND TARTARIC ACID INVOLVING HETEROCYCLIC ENOLATES WITH EXOCYCLIC DOUBLE-BONDS
SEEBACH, D
AEBI, JD
GANDERCOQUOZ, M
NAEF, R
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (04) : 1194 - 1216

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