A convenient method for the preparation of inverted tert-alkyl carboxylates from chiral tert-alcohols by a new type of oxidation-reduction, condensation using 2,6-dimethyl-1,4-benzoquinone

被引：74
作者：
Mukaiyama, T
Shintou, T
Fukumoto, K
机构：
[1] Kitasato Inst, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan
[2] Kitasato Univ, Inst Life Sci, Minato Ku, Tokyo 1088641, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 35期
关键词：
D O I：
10.1021/ja0303844
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxidation-reduction condensation using in situ-formed alkoxydiphenylphosphines, 2,6-dimethyl-1,4-benzoquinone, and carboxylic acids provided a new and efficient method for the preparation of inverted tert-alkyl carboxylates from various chiral tertiary alcohols. Copyright © 2003 American Chemical Society.
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收藏
页码：10538 / 10539
页数：2
相关论文
共 18 条
[1]  
CROWTHER GP, 1988, ORG SYNTH, V4, P259
[2]   A practical catalytic asymmetric addition of alkyl groups to ketones [J].
García, C ;
LaRochelle, LK ;
Walsh, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10970-10971
[3]   Development of new synthetic reagents in Mitsunobu-type reaction [J].
Itô, S .
YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2001, 121 (08) :567-583
[4]   NOVEL METHOD FOR PREPARATION OF ACID ANHYDRIDES BY MEANS OF TRANS-DIBENZOYLETHYLENE + TERTIARY PHOSPHINES [J].
KUWAJIMA, I ;
MUKAIYAMA, T .
JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (06) :1385-&
[5]   PREPARATION OF ESTERS PF PHOSPHORIC ACID BY REACTION OF TRIVALENT PHOSPHORUS COMPOUNDS WITH DIETHYL AZODICARBOXYLATE IN PRESENCE OF ALCOHOLS [J].
MITSUNOBU, O ;
YAMADA, M ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (04) :935-+
[6]   PREPARATION OF CARBOXYLIC ESTERS AND PHOSPHORIC ESTERS BY ACTIVATION OF ALCOHOLS [J].
MITSUNOBU, O ;
EGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (12) :3427-+
[7]   PREPARATION OF ESTERS OF CARBOXYLIC AND PHOSPHORIC ACID VIA QUATERNARY PHOSPHONIUM SALTS [J].
MITSUNOBU, O ;
YAMADA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) :2380-+
[8]  
MITSUNOBU O, 1992, ORG REACTIONS, V42, P335
[9]   Preparation of various carboxylic acid esters from bulky alcohols and carboxylic acids by a new type oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone [J].
Mukaiyama, T ;
Kikuchi, W ;
Shintou, T .
CHEMISTRY LETTERS, 2003, 32 (03) :300-301
[10]   NOVEL METHOD FOR PREPARATION OF ACID ANHYDRIDES BY MEANS OF DIPHENYLMERCURY AND TERTIARY PHOSPHINE [J].
MUKAIYAMA, T ;
KUWAJIMA, I ;
SUZUKI, Z .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (08) :2024-&
12