ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND PIPERIDINES BY NUCLEOPHILIC-ADDITION TO N-ACYLIMINIUM IONS BEARING PYRROLIDINE CHIRAL AUXILIARIES

被引：68

作者：

SUZUKI, H ^{[1
]}

AOYAGI, S ^{[1
]}

KIBAYASHI, C ^{[1
]}

机构：

[1] TOKYO COLL PHARM,HACHIOJI,TOKYO 19203,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 33期

关键词：

D O I：

10.1016/0040-4039(94)88092-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of carbon nucleophiles to cyclic N-acyliminium salts chirally modified by various optically active pyrrolidines leads to highly enantioselective synthesis of 2-substituted pyrrolidines and piperidines.

引用

页码：6119 / 6122

页数：4

共 50 条

[1] ASYMMETRIC ELECTROPHILIC ALPHA-AMIDOALKYLATION .10. A NEW CAMPHORIMIDE DERIVED CHIRAL AUXILIARY FOR THE ASYMMETRIC-SYNTHESIS WITH N-ACYLIMINIUM IONS - PREPARATION OF ARACEMIC 2-SUBSTITUTED PIPERIDINES
WANNER, KT
PAINTNER, FF
TETRAHEDRON, 1994, 50 (10) : 3113 - 3122
[2] AN ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES
MEYERS, AI
BURGESS, LE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 220 - ORGN
[3] ASYMMETRIC-SYNTHESIS OF CHIRAL AMINES VIA NUCLEOPHILIC-ADDITION TO FERROCENYLALKYL SUBSTITUTED IMINES
DAVID, DM
KANEMAGUIRE, LAP
PYNE, SG
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 390 (01) : C6 - C9
[4] Asymmetric Bronsted Acid Catalyzed Nucleophilic Addition to in situ Generated Chiral N-Acyliminium Ions
Rueping, Magnus
Nachtsheim, Boris J.
SYNLETT, 2010, (01) : 119 - 122
[5] CHIRAL N-ACYLIMINIUM IONS AS NEW TOOLS IN THE ASYMMETRIC-SYNTHESIS OF CNS-ACTIVE COMPOUNDS
WANNER, KT
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 2 (1-2) : 62 - 64
[6] Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions:: stereoselective synthesis of functionalized N-heterocycles
Vieira, Adriano S.
Ferreira, Fernando P.
Fiorante, Pedro F.
Guadagnin, Rafael C.
Stefani, Helia A.
TETRAHEDRON, 2008, 64 (15) : 3306 - 3314
[7] A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES
BURGESS, LE
MEYERS, AI
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06): : 1656 - 1662
[8] The addition of 2-tert-butyldimethylsilyloxyfuran to cyclic N-acyliminium ions containing cyclohexyl-based chiral auxiliaries
D'Oca, MGM
Pilli, RA
Vencato, I
TETRAHEDRON LETTERS, 2000, 41 (50) : 9709 - 9712
[9] Asymmetric synthesis of hydroxylated pyrrolidines, piperidines and related bioactive compounds:: From N-acyliminium chemistry to N-α-carbanion chemistry
Huang, Pei-Qiang
SYNLETT, 2006, (08) : 1133 - 1149
[10] NUCLEOPHILIC-ADDITION TO HOMOCHIRAL N-ACYLISOQUINOLINIUM SALTS - ASYMMETRIC-SYNTHESIS OF (+)-CARNEGINE
COMINS, DL
BADAWI, MM
HETEROCYCLES, 1991, 32 (10) : 1869 - 1873

← 1 2 3 4 5 →