A LOW-TEMPERATURE MITSUNOBU REACTION FOR THE INVERSION OF STERICALLY HINDERED SECONDARY ALCOHOLS

被引：9

作者：

COLEMAN, RS

GRANT, EB

机构：

[1] Department of Chemistry, Biochemistry University of South Carolina, Columbia

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)74402-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mitsunobu inversion of 1,1'-binaphthalenediol 3 with benzoic acid was studied, and the success of the reaction, was found to depend upon quantitative formation of bis-oxyphosphonium salt 6 at -23 degrees C, prior to S(N)2 displacement at 25 degrees C.

引用

页码：8341 / 8344

页数：4

共 9 条

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COLEMAN, RS
GRANT, EB
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[3] COLEMAN RS, 1994, J AM CHEM SOC, V116
[4] EFFECT OF THE ACIDIC COMPONENT ON THE MITSUNOBU INVERSION OF A STERICALLY HINDERED ALCOHOL
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[6] A MECHANISTIC STUDY OF THE MITSUNOBU ESTERIFICATION REACTION
HUGHES, DL
REAMER, RA
BERGAN, JJ
GRABOWSKI, EJJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) : 6487 - 6491
[7] EFFICACIOUS MODIFICATION OF THE MITSUNOBU REACTION FOR INVERSIONS OF STERICALLY HINDERED SECONDARY ALCOHOLS
MARTIN, SF
DODGE, JA
[J]. TETRAHEDRON LETTERS, 1991, 32 (26) : 3017 - 3020
[8] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS
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[J]. SYNTHESIS-STUTTGART, 1981, (01): : 1 - 28
[9] Weiss U, 1987, Fortschr Chem Org Naturst, V52, P1

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