Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds

被引：32

作者：

Blanchet, J

Bonin, M

Chiaroni, A

Micouin, L

Riche, C

Husson, HP

机构：

[1] Univ Paris 05, CNRS, Chim Therapeut Lab, UMR 8638,Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France

[2] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(99)00328-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient and scalable route to chiral non-racemic alpha-substituted propargylamines is described. The reaction pathway consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R-()-phenylglycinol, (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：2935 / 2938

页数：4

共 12 条

[1] BINGER P, 1963, ANGEW CHEM INT EDIT, V2, P686
[2] ENANTIOSELECTIVE SYNTHESIS OF PRIMARY AMINES VIA GRIGNARD ADDITIONS TO STEREOGENIC N-(ALPHA-PHENYL-BETA-(BENZYLOXY)ETHYL)NITRONES
CHANG, ZY
COATES, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (11) : 3475 - 3483
[3] ENANTIOSELECTIVE SYNTHESIS OF ALLYL-AMINES, PROPARGYL-AMINES, AND 4-EN-2-YNYL-AMINES VIA 1,2-ADDITION OF ORGANOCERIUM REAGENTS TO CHIRAL ALDEHYDE IMINES
ENDERS, D
SCHANKAT, J
[J]. HELVETICA CHIMICA ACTA, 1995, 78 (04) : 970 - 992
[4] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond
Enders, D
Reinhold, U
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (12) : 1895 - 1946
[5] LITHIUM ALKOXIDES OF CINCHONA ALKALOIDS AS CHIRAL CONTROLLERS FOR ENANTIOSELECTIVE ACETYLIDE ADDITION TO CYCLIC N-ACYL KETIMINES
HUFFMAN, MA
YASUDA, N
DECAMP, AE
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) : 1590 - 1594
[6] CRYSTAL AND MOLECULAR-STRUCTURE OF DYNEMICIN-A - A NOVEL 1,5-DIYN-3-ENE ANTITUMOR ANTIBIOTIC
KONISHI, M
OHKUMA, H
TSUNO, T
OKI, T
VANDUYNE, GD
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (09) : 3715 - 3716
[7] Asymmetric synthesis of alpha-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines
Maury, C
Gharbaoui, T
Royer, J
Husson, HP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3687 - 3693
[8] NEGISHI EI, 1980, ORGANOMETALLICS MAIN, P286
[9] SYNTHESIS, CARDIAC ELECTROPHYSIOLOGY, AND BETA-BLOCKING ACTIVITY OF NOVEL ARYLPIPERAZINES WITH POTENTIAL AS CLASS II/III ANTIARRHYTHMIC AGENTS
PHILLIPS, GB
MORGAN, TK
LUMMA, WC
GOMEZ, RP
LIND, JM
LIS, R
ARGENTIERI, T
SULLIVAN, ME
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (04) : 743 - 750
[10] Stereocontrolled preparation of cis- and trans-2,6-dialkylpiperidines via diastereoselective reaction of 1-aza-4-oxabicyclo[4.3.0]nonane derivatives with Grignard reagents
Poerwono, H
Higashiyama, K
Yamauchi, T
Kubo, H
Ohmiya, S
Takahashi, H
[J]. TETRAHEDRON, 1998, 54 (46) : 13955 - 13970

← 1 2 →