Premium
Diastereoselective Synthesis of Chiral Amidophosphonates by 1,5‐Asymmetric Induction
Author(s) -
CastelotDeliencourt Géraldine,
Roger Elisabeth,
Pannecoucke Xavier,
Quirion JeanCharles
Publication year - 2001
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 - 10.1002/1099-0690(200108)2001:16<3031::aid-ejoc3031>3.0.co;2-5
Subject(s) - chemistry , asymmetric induction , alkylation , enantioselective synthesis , chiral auxiliary , alkyl , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
We have investigated two simple diastereoselective syntheses of substituted β‐amidophosphonates. The first one involved a Michael addition to α,β‐unsaturated amides 6 and 8a − d , derived from chiral amino alcohols, and permitted the preparation of alkyl‐substituted derivatives 7 and 9a − d with high diastereoselectivities (up to 95%) with the aid of a 1,5‐asymmetric induction. The second one, involving 1,5‐inductive alkylation of chiral β‐amidophosphonates 14a − c , was promising in terms of the yields, but the diastereoselectivities were disappointing (up to 50%). Finally, removal of the chiral auxiliary afforded phosphonocarboxylic acid, able to provide access to a wide range of compounds of great interest for the synthesis of biologically active products.