Premium
A chiral synthesis of (2 S , 3 S )‐phenylalanine‐3‐ 2 H via boronic esters
Author(s) -
Matteson Donald S.,
Beedle Ellen C.,
Christenson Erik,
Dewey Michael A.,
Peterson Mark L.
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580250613
Subject(s) - chemistry , sodium azide , diastereomer , lithium (medication) , enantiomer , sodium chlorite , phenylalanine , azide , reagent , medicinal chemistry , enantiomeric excess , alcohol , sodium , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , amino acid , medicine , chlorine dioxide , endocrinology , biochemistry
Reduction of (s)‐pinanediol ( S )[(phenyl) (chloro)‐methyl]boronate (1) with lithium triethylborodeuteride yielded ( s )‐pinanediol ( R )‐[(phenyl)methyl]boronate‐α‐ 2 H (2). The chiral purity of 2 was measured via peroxidic oxidation to ( S )‐benzyl alcohol‐α‐ 2 H (3), which was analyzed with an NMR chiral shift reagent. (Dichloro‐methyl)lithium converted 2 to ( s )‐pinanediol (1 S ,2 S )‐1‐chloro‐2‐phenylethylboronate‐2‐ 2 H (4), which with sodium azide yielded ( s )‐pinanediol (1 R ,2 S )‐1‐azido‐2‐phenylethylboronate‐2‐ 2 H (5). (Dichloromethyl) lithium with 5 yielded ( s )‐pinanediol (1 S , 2 S ,3 S )‐1‐chloro‐2‐azido‐3‐phenylpropylboronate‐3‐ 2 H (6), which was oxidized by sodium chlorite to (2 S ,3 S )‐2‐azido‐3‐phenylacetic acid‐3‐ 2 H (7). Hydrogenation of 7 yielded (2 S ,3 S )‐phenylalanine‐3‐ 2 H (8) in high diastereomeric and enantiomeric purity.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom