A Tandem Conjugate Addition/Cyclization Protocol for the Asymmetric Synthesis of 2-Aryl-4-aminotetrahydroquinoline-3-carboxylic Acid Derivatives

被引：39
作者：
Davies, Stephen G. [1 ]
Mujtaba, Nadeam [1 ]
Roberts, Paul M. [1 ]
Smith, Andrew D. [1 ]
Thomson, James E. [1 ]
机构：
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 09期
关键词：
PARALLEL KINETIC RESOLUTION; DIELS-ALDER REACTION; HOMOCHIRAL LITHIUM AMIDES; FORMAL TOTAL-SYNTHESIS; BETA-AMINO ACIDS; CYCLIZATION-ELIMINATION REACTION; MARTINELLIC ACID; TETRAHYDROQUINOLINE DERIVATIVES; FACILE SYNTHESIS; ALPHA; BETA-UNSATURATED ESTERS;
D O I：
10.1021/ol9004118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Condensation of tert-butyl (E)-3-(2'-aminophenyl)propenoate with a range of aromatic and heteroaromatic aldehydes gives the corresponding imines as single diastereoisomers (>98% de). Addition of lithium (R)-N-benzyl-N-(alpha-methylbenzyl)amide initiates a tandem conjugate addition/cyclization reaction to generate 2-aryl-4-aminotetrahydroquinoline-3-carboxylic acid derivatives in >98% de, >98% ee and high isolated yield. Hydrogenolysis of an N(1)-Boc protected derivative allows selective cleavage of the N-benzyl-alpha-methylbenzyl protecting groups without compromise of the diastereo- or enantiopurity.
引用
收藏
页码：1959 / 1962
页数：4
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