syn-selective direct catalytic asymmetric Mannich-type reactions of hydroxyketones using Y{N(SiMe3)2}3/linked-BINOL complexes

Mari Sugita; Akitake Yamaguchi; Noriyuki Yamagiwa; Shinya Handa; Shigeki Matsunaga; Masakatsu Shibasaki

doi:10.1021/ol052384+

syn-selective direct catalytic asymmetric Mannich-type reactions of hydroxyketones using Y{N(SiMe3)2}3/linked-BINOL complexes

Org Lett. 2005 Nov 10;7(23):5339-42. doi: 10.1021/ol052384+.

Authors

Mari Sugita¹, Akitake Yamaguchi, Noriyuki Yamagiwa, Shinya Handa, Shigeki Matsunaga, Masakatsu Shibasaki

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 16268573
DOI: 10.1021/ol052384+

Abstract

[reaction, structure: see text] Chiral Y{N(SiMe3)2}3/linked-BINOL catalyst generated Y-enolate in situ from various hydroxyketones (R2 = aryl, heteroaryl). Beta-amino-alpha-hydroxy ketones (R1 = aryl, heteroaryl, alkenyl) were obtained syn-selectively (up to 96/4) in high ee (up to 98%) and good yield (up to 98% yield).