Enantioselective synthesis of trans-4-methylpipecolic acid

被引：26
作者：
Alegret, Carlos
Santacana, Ferran
Riera, Antoni
机构：
[1] IRB, URSA, PCB, Barcelona 08028, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 20期
关键词：
D O I：
10.1021/jo071220z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).
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收藏
页码：7688 / 7692
页数：5
相关论文
共 63 条
[1]  
Agami C, 2001, EUR J ORG CHEM, V2001, P2385
[2]   A convenient method for the efficient removal of ruthenium byproducts generated during olefin metathesis reactions [J].
Ahn, YM ;
Yang, K ;
Georg, GI .
ORGANIC LETTERS, 2001, 3 (09) :1411-1413
[3]   Enantioselective synthesis of unsaturated amino acids using p-methoxybenzylamine as an ammonia equivalent [J].
Alcón, M ;
Moyano, A ;
Pericàs, MA ;
Riera, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4639-4651
[4]   Stereodivergent syntheses of conduramines and aminocyclitols [J].
Alegret, Carlos ;
Benet-Buchholz, Jordi ;
Riera, Antoni .
ORGANIC LETTERS, 2006, 8 (14) :3069-3072
[5]   Improved preparation of β-hydroxy-α-amino acids:: direct formation of sulfates by sulfuryl chloride [J].
Alonso, M ;
Riera, A .
TETRAHEDRON-ASYMMETRY, 2005, 16 (23) :3908-3912
[6]   Practical, scalable, enantioselective synthesis of (2R,3R)-N-boc-2-amino-3-cyclohexyl-3-hydroxypropanoic acid [J].
Alonso, N ;
Santacana, F ;
Rafecas, L ;
Riera, A .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2005, 9 (05) :690-693
[7]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[8]   ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION [J].
BAILEY, PD ;
BROWN, GR ;
KORBER, F ;
REED, A ;
WILSON, RD .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1263-1282
[9]   ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION OF IMINES WITH DIENES [J].
BAILEY, PD ;
WILSON, RD ;
BROWN, GR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1337-1340
[10]   OXIDATION OF ALPHA,BETA-UNSATURATED ALDEHYDES [J].
BAL, BS ;
CHILDERS, WE ;
PINNICK, HW .
TETRAHEDRON, 1981, 37 (11) :2091-2096
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