Phase-Transfer-Catalyzed Asymmetric Alkylation of α-Benzoyloxy-β-keto Esters: Stereoselective Construction of Congested 2,3-Dihydroxycarboxylic Acid Esters

被引：21

作者：

Hashimoto, Takuya ^{[1
]}

Sasaki, Keigo ^{[1
]}

Fukumoto, Kazuhiro ^{[1
]}

Murase, Yuichi ^{[1
]}

Abe, Naoyuki ^{[1
]}

Ooi, Takashi ^{[2
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

[2] Nagoya Univ, Dept Appl Chem, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2010年 / 5卷 / 03期

关键词：

alkylation; asymmetric synthesis; diastereoselectivity; hydroxylation; phase-transfer catalysis; QUATERNARY STEREOCENTERS; DICARBONYL COMPOUNDS; ATOM-TRANSFER; HYDROXYLATION; AMINO; KETOESTERS; MOLECULES; REAGENTS;

D O I：

10.1002/asia.200900344

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective phase-transfer-catalyzed alkylation of tert-butyl 2-benzoyloxy-3-oxobutanoate was realized by the use of an N-spiro chiral quaternary ammonium salt, as a complementary approach to the asymmetric hydroxylation of alpha-alkyl-beta-keto esters. The synthetic utility of the alkylated compounds is highlighted by the diastereoselective reduction and alkylation of the remaining ketone moiety to give various enantiomerically enriched congested 2,3-dihydroxy-carboxylic acid esters.

引用

页码：562 / 570

页数：9

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