Asymmetric Rh(I)-Catalyzed Addition of MIDA Boronates to N-tert-Butanesulfinyl Aldimines: Development and Comparison to Trifluoroborates

被引：53

作者：

Brak, Katrien ^{[1
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 09期

基金：

美国国家科学基金会;

关键词：

ELECTROPHILIC DISPLACEMENT REACTIONS; SMALL-MOLECULE SYNTHESIS; RH-CATALYZED ARYLATION; GENERATED IN-SITU; ARYLBORONIC ACIDS; BORONIC ACIDS; ARENEBORONIC ACIDS; COUPLING REACTIONS; ARYL HALIDES; TOSYLARYLIMINES;

D O I：

10.1021/jo100318s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(I)-catalyzed addition of alkenyl and aryl MIDA boronates to N-tert-butanesulfinyl aromatic and aliphatic imines proceeds in good yields (up to 99%) and with very high selectivity (98:2 to > 99:1). In comparison to trifluoroborates, higher yields and selectivities are observed for the addition to N-tert-butanesulfinyl aromatic imines. This new method expands upon the versatility of the Rh(I)-catalyzed addition of boron reagents to imines, thereby further enabling the synthesis of chiral alpha-branched amines.

引用

页码：3147 / 3150

页数：4

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