Catalytic Enantioselective Protonation of α‐Oxygenated Ester Enolates Prepared through Phospha‐Brook Rearrangement | Zendy

Hayashi Masashi | Zendy; Nakamura Shuichi | Zendy

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Catalytic Enantioselective Protonation of α‐Oxygenated Ester Enolates Prepared through Phospha‐Brook Rearrangement

Author(s) -

Hayashi Masashi,

Nakamura Shuichi

Publication year - 2011

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.201007568

Subject(s) - enantioselective synthesis , protonation , catalysis , chemistry , enantiomer , cinchona , organic chemistry , medicinal chemistry , cinchona alkaloids , ion

Phosphonates go chiral : The organocatalytic enantioselective reaction of α‐ketoesters with phosphites using cinchona alkaloids and Na 2 CO 3 has afforded α‐phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol % does not result in a significant decrease of the enantioselectivity.

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