Reaction of the lithio-derivative of methoxy allene with SAMP-hydrazones:: Access to enantiopure 3-pyrrolines

被引：39

作者：

Breuil-Desvergnes, V ^{[1
]}

Compain, P ^{[1
]}

Vatèle, JM ^{[1
]}

Goré, J ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, Lab Chim Organ 1, CPE Lyon, F-69622 Villeurbanne, France

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(99)00934-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Lithio methoxy allene reacts with SAMP-hydrazones to give alpha-allenyl hydrazines 5 or 3-methoxy-3-pyrrolines 6 depending on the nature of the solvent. Both compounds have been obtained with d.e. greater than or equal to 99%. Hydrogenolysis of the N-N bond of 6 affords the pyrroline 7 in enantiopure form. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5009 / 5012

页数：4

共 10 条

[1] Stereochemistry .87. Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route
Balasubramanian, T
Hassner, A
[J]. TETRAHEDRON LETTERS, 1996, 37 (32) : 5755 - 5758
[2] ALLENES AND ACETYLENES .18. SYNTHESIS OF 3-PYRROLINES BY SILVER(I)-CATALYZED CYCLIZATION OF ALLENIC AMINES
CLAESSON, A
SAHLBERG, C
LUTHMAN, K
[J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (04): : 309 - 310
[3] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED PRIMARY AMINES BY NUCLEOPHILIC-ADDITION TO ALDEHYDE-SAMP HYDRAZONES
ENDERS, D
SCHUBERT, H
NUBLING, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (12): : 1109 - 1110
[4] Enders D, 1997, SYNLETT, P355
[5] Enders D, 1997, LIEBIGS ANN-RECL, P1115
[6] 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
[7] Ishii K, 1999, SYNLETT, P228
[8] ROCHET P, 1993, SYNLETT, P105
[9] Enantioselective synthesis of (+)-goniodiol and of its naturally occurring acetylated analogs
Surivet, JP
Gore, J
Vatele, JM
[J]. TETRAHEDRON, 1996, 52 (47) : 14877 - 14890
[10] Phosphine-catalyzed [3+2] cycloaddition reaction of methyl 2,3-butadienoate and N-tosylimines. A novel approach to nitrogen heterocycles
Xu, ZR
Lu, XY
[J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3461 - 3464

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