Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins

被引：224

作者：

Luppi, G

Cozzi, PG

Monari, M

Kaptein, B

Broxterman, QB

Tomasini, C

机构：

[1] Univ Bologna, Alma Mater Studiorum, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

[2] DSM Res BV, Adv Synth & Catalysis, Life Sci, NL-6160 MD Geleen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 18期

关键词：

D O I：

10.1021/jo050257l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol condensation of acetone with several isatins is described. The desired compound was obtained in quantitative yield and with good enantioselectivities up to 77%. The best results were obtained with 10 mol % H-D-Pro-L-beta(3)-hPhg-OBn as a catalyst, resulting in the preferential formation of the (R)-enantiomer. The absolute configuration of the newly formed chiral center has been assigned by an X-ray diffraction study and CD spectra analysis of the molecules.

引用

页码：7418 / 7421

页数：4

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