Premium
Synthesis and Ruthenium‐Catalyzed Enantioselective Hydrogenation of 3‐ O ‐Substituted 1,3‐Dihydroxypropan‐2‐ones. Part 2
Author(s) -
Cesarotti Edoardo,
Antognazza Patrizia,
Pallavicini Marco,
Villa Luigi
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760620
Subject(s) - chemistry , enantioselective synthesis , ruthenium , catalysis , noyori asymmetric hydrogenation , combinatorial chemistry , asymmetric hydrogenation , organic chemistry , stereochemistry , medicinal chemistry
A number of 3‐ O ‐substituted 1,3‐dihydroxypropan‐2‐ones have been synthesized in view of their potential use as prochiral precursors of optically active glycerols. Indeed, the oxo‐ethers have been reduced to the corresponding 3‐ O ‐substituted glycerols via chiral Ru complexes derived from ( S )‐binap, ( =(−)‐( S )‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthalene) with enantiomeric excesses up to 93%. The steric course of the catalytic reduction appears to be essentially dependent on the steric encumbrance of the substituents; indeed, a dramatic increase of the enantiomeric excess is observed when the bulky trityl group is substituted by the less encumbering benzyl or octadecyl groups.