Phase‐Transfer‐Catalyzed Asymmetric Michael Addition of (Iminomethyl)phosphonates to α,β‐Unsaturated Ketones: Access to α‐Aminophosphonic Acid Derivatives | Zendy

Li JinShan | Zendy; Cui HanFeng | Zendy; Zhang KeFeng | Zendy; Nie Jing | Zendy; Ma JunAn | Zendy

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Phase‐Transfer‐Catalyzed Asymmetric Michael Addition of (Iminomethyl)phosphonates to α,β‐Unsaturated Ketones: Access to α‐Aminophosphonic Acid Derivatives

Author(s) -

Li JinShan,

Cui HanFeng,

Zhang KeFeng,

Nie Jing,

Ma JunAn

Publication year - 2017

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201700249

Subject(s) - chemistry , michael reaction , catalysis , adduct , yield (engineering) , salt (chemistry) , phase transfer catalyst , organic chemistry , medicinal chemistry , ammonium , materials science , metallurgy

A phase‐transfer‐catalyzed asymmetric Michael addition of (iminomethyl)phosphonates to α,β‐unsaturated ketones is described. In the presence of 1 mol‐% of a chiral dinuclear N ‐spiro ammonium salt, the addition reaction proceeded smoothly to afford the adducts in up to 97 % yield with up to 99:1 dr and 78 % ee . One of the products was readily converted into a cyclic α‐aminophosphonic acid derivative without any erosion of the enantiopurity.

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