Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines:: (+)-dihydropinidine

被引:72
作者
Davis, FA [1 ]
Szewczyk, JM [1 ]
机构
[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
关键词
D O I
10.1016/S0040-4039(98)01223-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New methodology for the enantioselective synthesis of stable;N-protected beta-amino aldehydes 5 and 6, and their application to the asymmetric synthesis of (+)-2-phenylpiperdine (11) and (+)-dihydropinidine (14) is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5951 / 5954
页数:4
相关论文
共 44 条
[1]  
Angle S. R., 1995, STUD NAT PROD CHEM, V16, P453
[2]  
[Anonymous], 1996, Adv. Nitrogen Heterocycl
[3]  
[Anonymous], 1985, ALKALOIDS CHEM BIOL
[4]   Asymmetric routes to substituted piperidines [J].
Bailey, PD ;
Millwood, PA ;
Smith, PD .
CHEMICAL COMMUNICATIONS, 1998, (06) :633-640
[5]   Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route [J].
Balasubramanian, T ;
Hassner, A .
TETRAHEDRON LETTERS, 1996, 37 (32) :5755-5758
[6]   SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].
BALIAH, V ;
JEYARAMAN, R ;
CHANDRASEKARAN, L .
CHEMICAL REVIEWS, 1983, 83 (04) :379-423
[7]  
BUBBERT C, 1994, SYNLETT, P675
[8]   SYNTHETIC APPROACHES TOWARDS MANZAMINE - AN EASY PREPARATION OF BETA-AMINO ALDEHYDES [J].
CHESNEY, A ;
MARKO, IE .
SYNTHETIC COMMUNICATIONS, 1990, 20 (20) :3167-3180
[9]   STEREOCONTROLLED PREPARATION OF CIS-2,6-DIALKYLPIPERIDINE AND TRANS-2,6-DIALKYLPIPERIDINE VIA 1-ACYLDIHYDROPYRIDINE INTERMEDIATES - SYNTHESIS OF (+/-)-SOLENOPSIN-A AND (+/-)-DIHYDROPINIDINE [J].
COMINS, DL ;
WEGLARZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2506-2512
[10]   Iodomethylation of chiral alpha-amino aldehydes by means of samarium/diiodomethane. Application to the synthesis of various enantiomerically pure compounds [J].
Concellon, JM ;
Bernad, PL ;
PerezAndres, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8902-8906