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Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition

Author:
Wujkowska, Zuzanna, Zawisza, Anna, Leśniak, Stanisław, Rachwalski, Michał
Source:
Tetrahedron 2019 v.75 no.2 pp. 230-235
ISSN:
0040-4020
Subject:
aldehydes, chemical reactions, chemical structure, diastereoselectivity, enantioselectivity, ethyleneimine, organocatalysts, oxides, phosphine
Abstract:
A series of new optically pure phosphine oxides containing chiral aziridine subunit were synthesized in good yields and applied as organocatalysts in asymmetric Michael reaction of various aliphatic aldehydes with β-nitrostyrene. The corresponding organocatalysts were synthesized starting from optically pure aziridines in a few simple efficient steps. The appropriate Michael adducts were obtained in most cases in very high chemical yield (up to 97%), excellent enantioselectivity (up to 98% of ee) and diastereoselectivity (up to 95:5 of dr).
Agid:
6251138