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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 33期

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

页码：5951 / 5954

页数：4

共 44 条

[21] Davis FA, 1998, CHEM SOC REV, V27, P13
[22] Asymmetric Strecker synthesis using enantiopure sulfinimines and diethylaluminum cyanide: The alcohol effect
Davis, FA
Portonovo, PS
Reddy, RE
Chiu, YH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 440 - 441
[23] ASYMMETRIC-SYNTHESIS OF (R)-(+)-BETA-PHENYLALANINE FROM (S)-(+)-BENZYLIDENE-P-TOLUENESULFINAMIDE - REGENERATION OF THE SULFINIMINE PRECURSOR
DAVIS, FA
REDDY, RE
SZEWCZYK, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 7037 - 7039
[24] ASYMMETRIC RING-CLOSURE REACTIONS MEDIATED BY A CHIRAL C-2 SYMMETRICAL ORGANOSELENIUM REAGENT
DEZIEL, R
MALENFANT, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (14) : 4660 - 4662
[25] Switchover of diastereofacial selectivity in the condensation reaction of optically active N-sulfinimine with ester enolate
Fujisawa, T
Kooriyama, Y
Shimizu, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (22) : 3881 - 3884
[26] THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS
HART, DJ
HA, DC
[J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1447 - 1465
[27] Asymmetric synthesis of amines using a chiral, non-racemic, benzylidene sulfinamide derived from a recoverable precursor
Hose, DRJ
Mahon, MF
Molloy, KC
Raynham, T
Wills, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07): : 691 - 703
[28] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS VIA CHIRAL N-ALKYLIDENESULFINAMIDES
HUA, DH
LAGNEAU, N
WANG, H
CHEN, JS
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 349 - 352
[29] AN ENANTIOSPECIFIC SYNTHESIS OF SOLENOPSIN-A
JEFFORD, CW
WANG, JB
[J]. TETRAHEDRON LETTERS, 1993, 34 (18) : 2911 - 2914
[30] APPROACHES TOWARD THE TOTAL SYNTHESES OF ASTIN-A, ASTIN-B, AND ASTIN-C
JIANG, JJ
SCHUMACHER, KK
JOULLIE, MM
DAVIS, FA
REDDY, RE
[J]. TETRAHEDRON LETTERS, 1994, 35 (14) : 2121 - 2124

← 1 2 3 4 5 →