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Asymmetric Synthesis of α ‐Substituted β ‐Nitrophosphonic Acids by Phospha‐Analogous Michael Addition to Aromatic Nitroalkenes
Author(s) -
Enders Dieter,
Tedeschi Livio,
Bats Jan Willem
Publication year - 2000
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 - 10.1002/1521-3773(20001215)39:24<4605::aid-anie4605>3.0.co;2-x
Subject(s) - michael reaction , bifunctional , nucleophile , enantioselective synthesis , chemistry , nucleophilic addition , asymmetric induction , organic chemistry , stereochemistry , catalysis
Asymmetric C−P bond formation through phospha‐analogous Michael addition to nitroalkenes leads with high asymmetric induction to α ‐substituted β ‐nitrophosphonic acids [Eq. (1)], which constitute valuable bifunctional synthetic building blocks and direct precursors to β ‐aminophosphonic acids. The key to success is a P nucleophile based on an easily removable TADDOL auxiliary.