On the possibility of carbamate-directed hydroboration. An approach to the asymmetric synthesis of 1-aminocyclopentane-1,3-dicarboxylic acid

被引：24
作者：
Hodgson, DM
Thompson, AJ
Wadman, S
Keats, CJ
机构：
[1] Univ Oxford, Dept Chem, Dyson Perrins Lab, Oxford OX1 3QY, England
[2] Glaxo Wellcome Med Res Ctr, Stevenage SG1 2NY, Herts, England
[3] Univ Oxford, Dept Chem, Chem Crystallog Lab, Oxford OX1 3PD, England
来源：
TETRAHEDRON | 1999年 / 55卷 / 35期
基金：
英国工程与自然科学研究理事会;
关键词：
amino acids and derivatives; carbamates; cycloalkenes; hydroboration;
D O I：
10.1016/S0040-4020(99)00596-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Hydroboration (using BH3) of 1-substituted 3-cyclopentenes 3, 9 and 17 and an enantioselective synthesis of the excitatory amino acid 1-aminocyclopentane-1,3-dicarboxylic acid via asymmetric hydroboration [90% de, 45% ee using (+)-IpcBH(2)] of cyclopentene 17 are described. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：10815 / 10834
页数：20
相关论文
共 46 条
[1]   SIR92 - a program for automatic solution of crystal structures by direct methods [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, G ;
GUAGLIARDI, A ;
BURLA, MC ;
POLIDORI, G ;
CAMALLI, M .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435
[2]   Hydroborations catalysed by transition metal complexes [J].
Beletskaya, I ;
Pelter, A .
TETRAHEDRON, 1997, 53 (14) :4957-5026
[3]   HYDROBORATION OF TERPENES .9. A SIMPLE IMPROVED PROCEDURE FOR UPGRADING THE OPTICAL PURITY OF COMMERCIALLY AVAILABLE ALPHA-PINENES AND BETA-PINENES - CONVERSION OF (+)-ALPHA-PINENE TO (+)-BETA-PINENE VIA HYDROBORATION ISOMERIZATION [J].
BROWN, HC ;
JOSHI, NN .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4059-4062
[4]   HYDROBORATION .46. REGIOCHEMISTRY AND STEREOCHEMISTRY OF HYDROBORATION OF REPRESENTATIVE CYCLIC OLEFINS WITH 9-BORABICYCLO[3.3.1]NONANE [J].
BROWN, HC ;
LIOTTA, R ;
BRENER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3427-3432
[5]   VERSATILE ALPHA-PINENE-BASED BORANE REAGENTS FOR ASYMMETRIC SYNTHESES [J].
BROWN, HC ;
RAMACHANDRAN, PV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :1-19
[6]   SIMPLE SYNTHESIS OF MONOISOPINOCAMPHEYLBORANE OF HIGH OPTICAL PURITY [J].
BROWN, HC ;
SCHWIER, JR ;
SINGARAM, B .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (22) :4395-4397
[7]   ENANTIOSELECTIVE HYDROBORATIONS CATALYZED BY RHODIUM(+1) COMPLEXES [J].
BURGESS, K ;
VANDERDONK, WA ;
OHLMEYER, MJ .
TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :613-621
[8]   WEIGHTING SCHEME FOR LEAST-SQUARES STRUCTURE REFINEMENT [J].
CARRUTHERS, JR ;
WATKIN, DJ .
ACTA CRYSTALLOGRAPHICA SECTION A, 1979, 35 (JUL) :698-699
[9]  
Cromer D. T., 1974, INT TABLES XRAY CRYS, V4
[10]   SYNTHESIS, RESOLUTION, AND ABSOLUTE-CONFIGURATION OF THE ISOMERS OF THE NEURONAL EXCITANT 1-AMINO-1,3-CYCLOPENTANEDICARBOXYLIC ACID [J].
CURRY, K ;
PEET, MJ ;
MAGNUSON, DSK ;
MCLENNAN, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :864-867
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