Premium
Preparation of α‐Amino Acids by Oxidative Oxazoline–Oxazinone Rearrangement–Hydrogenation (OOOH). Scope and Limitations
Author(s) -
Liu Chaomin,
Molinski Tadeusz F.
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100452
Subject(s) - oxazoline , chemistry , oxidative phosphorylation , amino acid , combinatorial chemistry , asymmetric hydrogenation , ab initio , scope (computer science) , organic chemistry , enantioselective synthesis , computational chemistry , stereochemistry , catalysis , biochemistry , computer science , programming language
The range and scope of the oxidative oxazoline–oxazinone rearrangement–hydrogenation sequence (OOOH)—a short, direct asymmetric synthesis of α‐amino acids from carboxylic acids—was explored. The highest yet reported diastereoselectivity for hydrogenation of the oxazinone CN bond (d.r.=>80:1) is disclosed and rationalized with the aid of ab initio molecular calculations.