Synthesis of optically active α-amino esters via dynamic kinetic resolution:: A mechanistic study

被引：61

作者：

Ben, RN

Durst, T ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

[2] SUNY Binghamton, Dept Chem, Binghamton, NY 13902 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 21期

关键词：

D O I：

10.1021/jo9811625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of N-protected optically active alpha-amino esters from racemic alpha-halo esters via dynamic kinetic resolution (DKR) mill be described. This methodology is general in nature and provides the desired optically active N-protected amino esters in 70-95% yield with diastereomeric excesses in the range of 85 to >98%. Applications and mechanistic aspects mill be discussed.

引用

页码：7700 / 7706

页数：7

共 22 条

[1] MOLECULAR MECHANICS (MM3) CALCULATIONS ON ALDEHYDES AND KETONES
ALLINGER, NL
CHEN, KS
RAHMAN, M
PATHIASERIL, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (12) : 4505 - 4517
[2] BEN RN, UNPUB
[3] ALPHA-HYDROXY ESTERS AS INEXPENSIVE CHIRAL AUXILIARIES IN RHODIUM(II)-CATALYZED CYCLOPROPANATIONS WITH VINYLDIAZOMETHANES
DAVIES, HML
CANTRELL, WR
[J]. TETRAHEDRON LETTERS, 1991, 32 (45) : 6509 - 6512
[4] ASYMMETRIC-SYNTHESIS OF ALPHA-HALO ESTERS
DURST, T
KOH, K
[J]. TETRAHEDRON LETTERS, 1992, 33 (45) : 6799 - 6802
[5] EFFICIENT ALPHA-HALOGENATION OF ACYL CHLORIDES BY N-BROMOSUCCINIMIDE, N-CHLOROSUCCINIMIDE, AND MOLECULAR IODINE
HARPP, DN
BAO, LQ
BLACK, CJ
GLEASON, JG
SMITH, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23) : 3420 - 3427
[6] Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[7] REACTION OF (R)-PANTOLACTONE ESTERS OF ALPHA-BROMOACIDS WITH AMINES - A REMARKABLE SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-AMINO ESTERS
KOH, K
BEN, RN
DURST, T
[J]. TETRAHEDRON LETTERS, 1993, 34 (28) : 4473 - 4476
[8] A FACILE SYNTHESIS OF OPTICALLY-ACTIVE C-2-SYMMETRICAL 2,5-DISUBSTITUTED PYRROLIDINES AND OTHER BETA,BETA'-DIHYDROXYAMINES
KOH, K
BEN, RN
DURST, T
[J]. TETRAHEDRON LETTERS, 1994, 35 (03) : 375 - 378
[9] STEREOSELECTIVE S(N)2 REACTIONS OF THE (R)-PANTOLACTONE ESTER OF RACEMIC ALPHA-HALO CARBOXYLIC-ACIDS WITH ARYLOXIDES - A SYNTHESIS OF (S)-2-ARYLOXY AND (S)-2-HYDROXY ACIDS
KOH, K
DURST, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) : 4683 - 4686
[10] Dynamic kinetic resolution utilizing 2-oxoimidazolidine-4-carboxylate as a chiral auxiliary: Stereoselective alkylation of alpha-bromo amides with malonic ester enolates
Kubo, A
Kubota, H
Takahashi, M
Nunami, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 5830 - 5837

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