Direct Catalytic Asymmetric Mannich-Type Reaction of α-N3 Amide

Zhongdong Sun; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/chem.201503921

Direct Catalytic Asymmetric Mannich-Type Reaction of α-N3 Amide

Chemistry. 2015 Dec 1;21(49):17574-7. doi: 10.1002/chem.201503921. Epub 2015 Oct 20.

Authors

Zhongdong Sun¹, Karin Weidner¹, Naoya Kumagai², Masakatsu Shibasaki³

Affiliations

¹ Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan).
² Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan). mshibasa@bikaken.or.jp.
³ Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan). nkumagai@bikaken.or.jp.

PMID: 26439589
DOI: 10.1002/chem.201503921

Abstract

An α-N3 7-azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich-type reaction with N-thiophosphinoyl imines by the action of a cooperative catalyst. The thus-obtained highly enantioenriched anti-adduct was transformed into β-amino-α-azido acid in high yield by simple acidic treatment.

Keywords: Mannich; amide; asymmetric catalysis; azide; enantioselective.

Publication types

Research Support, Non-U.S. Gov't