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First and Highly Stereoselective Synthesis of Both Enantiomers of Octahydroindole‐2‐phosphonic Acid (Oic P )
Author(s) -
ViverosCeballos José Luis,
MartínezToto Erick Iván,
EustaquioArmenta César,
Cativiela Carlos,
Ordóñez Mario
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.201701330
Subject(s) - chemistry , stereoselectivity , bicyclic molecule , kinetic resolution , enantiomer , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
We report the first stereoselective synthesis of (2 R ,3a R ,7a R )‐ and (2 S ,3a S ,7a S )‐octahydroindole‐2‐phosphonic acid 2 (Oic P derivatives). The key points are the highly diastereoselective synthesis of cis ‐fused bicyclic (3a R ,7a R )‐ and (3a S ,7a S )‐pyrrolidin‐2‐ones 4 through a dynamic kinetic resolution of racemic γ‐keto acid (±)‐ 5 with ( R )‐ and ( S )‐phenylglycinol via Meyers' bicyclic lactams, and the highly diastereoselective addition of trimethyl phosphite to the N ‐acyliminium ions 3 obtained from 4 .