Diastereoselective Synthesis of ß-Lactam-Oxindole Hybrids Through a Three-Component Reaction of Azetidine-2,3-diones, a-Diazo-oxindoles, and Alcohols Catalyzed by [Rh2(OAc)4]

被引：37

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Aragoncillo, Cristina ^{[1
]}

Callejo, Ricardo ^{[1
]}

Pilar Ruiz, M. ^{[1
]}

Rosario Torres, M. ^{[3
]}

机构：

[1] Univ Complutense Madrid, Grp Lactamas & Heterociclos Bioactivos, Dept Quim Organ 1, Unidad Asociada CSIC,Fac Quim, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

[3] Univ Complutense Madrid, Lab Difracc Rayos X, Fac Quim, E-28040 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 12期

关键词：

Multicomponent reactions; Nitrogen heterocycles; Lactams; Diazo compounds; Ylides; Rhodium; C BOND FORMATION; ASYMMETRIC-SYNTHESIS; RING EXPANSION; OXONIUM YLIDE; BETA-LACTAM; MULTICOMPONENT REACTIONS; ISATINS; EFFICIENT; REARRANGEMENT; ALLYLATION;

D O I：

10.1002/ejoc.201101625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Lactamoxindole hybrids have been synthesized in good yields in a one-pot procedure through efficient and stereoselective capture of an oxonium ylide with azetidine-2,3-diones. The reaction allows high to moderate control of stereoselectivity, depending on the 3-diazo-oxindole precursor and the hydroxylic compound used. Two new quaternary stereogenic centers were formed; the stereochemistry at the C-3 quaternary center was controlled by a bulky substituent at C-4, whereas the stereoselectivity in the adjacent second quaternary stereogenic center was controlled by the a-diazo-oxindole. The stereochemistry of both quaternary centers has been unambiguously assigned by single-crystal X-ray diffraction.

引用

页码：2359 / 2366

页数：8

共 61 条

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