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The First Highly Enantioselective Alkynylation of Chloral: A Practical and Efficient Pathway to Chiral Trichloromethyl Propargyl Alcohols
Author(s) -
Jiang Biao,
Si YuGui
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200303237
Subject(s) - chemistry , enantioselective synthesis , chloral , yield (engineering) , alkynylation , propargyl , enantiomer , adduct , propargyl alcohol , enantiomeric excess , ligand (biochemistry) , organic chemistry , alcohol , catalysis , biochemistry , materials science , receptor , metallurgy
A new, inexpensive chiral amino alcohol‐based ligand, (1 S ,2 S )‐2‐ N,N ‐dimethylamino‐1‐(4‐nitrophenyl)‐3‐( tert ‐butyloxy)propan‐1‐ol, was developed for the asymmetric alkynylation of chloral in high yield with up to 98% ee. The resulting chiral adduct ( S )‐1‐trichloromethyl‐3‐phenyl‐2‐propyn‐1‐ol was hydrogenated over 10% Pd/C to give the useful intermediate chiral trichloromethyl carbinol in quantitative yield, which was efficiently transformed into the pharmaceutically important building blocks 2‐hydroxy‐4‐phenylbutanoate and homophenylalanine in high yield with excellent enantiomeric excess.