Catalyst‐Enabled Site‐Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors | Zendy

Uraguchi Daisuke | Zendy; Shibazaki Ryo | Zendy; Tanaka Naoya | Zendy; Yamada Kohei | Zendy; Yoshioka Ken | Zendy; Ooi Takashi | Zendy

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Catalyst‐Enabled Site‐Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors

Author(s) -

Uraguchi Daisuke,

Shibazaki Ryo,

Tanaka Naoya,

Yamada Kohei,

Yoshioka Ken,

Ooi Takashi

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201800057

Subject(s) - stereoselectivity , chemistry , enantioselective synthesis , reactivity (psychology) , cinchonidine , protonation , michael reaction , conjugated system , catalysis , organocatalysis , cinchona , adduct , stereochemistry , lewis acids and bases , thiourea , organic chemistry , polymer , medicine , ion , alternative medicine , pathology

A site‐divergent stereoselective Michael reaction system is developed based on the identification of two distinct catalysts. Cinchonidine‐derived thiourea catalyzes the 1,4‐addition of prochiral azlactone enolates to enynyl N ‐acyl pyrazoles in a highly diastereo‐ and enantioselective manner to give stereochemically defined alkynes, while P ‐spiro chiral triaminoiminophosphorane catalytically controls the stereoselective 1,6‐addition and the consecutive γ‐protonation of the vinylogous enolate intermediate to afford Z , E ‐configured conjugated dienes. This 1,6‐adduct serves as a valuable precursor for the synthesis of a 2‐amino‐2‐deoxy sugar.

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