Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis ofC- andP-Chiral Phosphoramidates | Zendy

Yasunori Toda | Zendy; Maren Pink | Zendy; Jeffrey N. Johnston | Zendy

Open Access

Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis ofC- andP-Chiral Phosphoramidates

Author(s) -

Yasunori Toda,

Maren Pink,

Jeffrey N. Johnston

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5088584

Subject(s) - enantioselective synthesis , chemistry , brønsted–lowry acid–base theory , catalysis , halogen , organic chemistry , combinatorial chemistry , alkyl

The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral centers, carbon and phosphorus, leading to cyclic P-chiral phosphoramidates. In addition to their inherent value, the phosphoramidates are precursors to enantioenriched epoxy allylamines.

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