Asymmetric synthesis of silylated α-amino acid esters through dynamic kinetic resolution

被引：23

作者：

Chen, JX ^{[1
]}

Tunge, JA ^{[1
]}

Norton, JR ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 12期

关键词：

D O I：

10.1021/jo010940h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Esters of three types of silylated alpha-amino acids have been prepared from appropriate zirconaaziridines. Slow addition (syringe pump) of the (R,R) carbonate of transstilbene gave metallacycles with the maximum possible diastereomeric excess (as determined by the diastereomeric excess produced by the Hoffmann test-the same reaction but with racemic carbonate). Methanolysis gave esters (RO2C)CH(R')(NHPh) (R' = Me3Si, Me3SiCH2, and p-Me-3-SiC6H4) with the same optical purity at the alpha carbon.

引用

页码：4366 / 4369

页数：4

共 50 条

[1] Rhodium-catalyzed asymmetric hydrogenation through dynamic kinetic resolution:: asymmetric synthesis of anti-β-hydroxy-α-amino acid esters
Makino, K
Fujii, T
Hamada, Y
TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 481 - 485
[2] Dynamic Kinetic Resolution of L-Threonine-derived α-Bromo Esters for Asymmetric Synthesis of α-Amino Esters
Kim, Yelim
Park, Kon Ji
Lee, Myung-su
Ryu, Hyejin
Park, Yong Sun
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (01): : 265 - 268
[3] Asymmetric synthesis of amino acid derivatives through the dynamic kinetic resolution of zircononcene imine complexes.
Tunge, JA
Norton, JR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U4 - U4
[4] Asymmetric Synthesis of anti-β-Amino-α-Hydroxy Esters via Dynamic Kinetic Resolution of β-Amino-α-Keto Esters
Goodman, C. Guy
Do, Dung T.
Johnson, Jeffrey S.
ORGANIC LETTERS, 2013, 15 (10) : 2446 - 2449
[5] Dynamic kinetic resolution of α-amino acid esters in the presence of aldehydes
Schichl, Daniel A.
Enthaler, Stephan
Holla, Wolfgang
Riermeier, Thomas
Kragl, Udo
Beller, Matthias
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (20) : 3506 - 3512
[6] Synthesis of α-amino esters by dynamic kinetic resolution of α-haloacyl imidazolidinones
Caddick, S
Afonso, CAM
Candeias, SX
Hitchcock, PB
Jenkins, K
Murtagh, L
Pardoe, D
Santos, AG
Treweeke, NR
Weaving, R
TETRAHEDRON, 2001, 57 (30) : 6589 - 6605
[7] Asymmetric Synthesis of N-Alkyl Amino Acids through a Biocatalytic Dynamic Kinetic Resolution of PEGylated N-Alkyl Amino Esters
Molinaro, Carmela
Kelly, Sean
Tang, Allison
Iding, Hans
Stocker, Patrik
Xin, Linghu
Gosselin, Francis
ORGANIC LETTERS, 2023, 25 (49) : 8927 - 8931
[8] Dynamic kinetic resolution of α-bromo carboxylic acid derivatives in asymmetric nucleophilic substitution with chiral α-amino esters
Chang, JY
Shin, EK
Kim, HJ
Kim, Y
Park, YS
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (06): : 989 - 992
[9] Asymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters
Steward, Kimberly M.
Corbett, Michael T.
Goodman, C. Guy
Johnson, Jeffrey S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (49) : 20197 - 20206
[10] Asymmetric formation of α-amino acid esters through dynamic kinetic resolution:: A cyclic carbonate as an optically active CO2 synthon
Tunge, JA
Gately, DA
Norton, JR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) : 4520 - 4521

← 1 2 3 4 5 →