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Optically Active t‐Butyl 2‐(p‐Tolylsulfinyl)propionate and ‐butyrate: Synthesis and Reactivity in Aldol‐type Condensations
Author(s) -
Solladié Guy,
MatloubiMoghadam Firouz,
Luttmann Claude,
Mioskowski Charles
Publication year - 1982
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.19820650533
Subject(s) - chemistry , butyrate , aldol condensation , steric effects , propionate , aldol reaction , optically active , reactivity (psychology) , yield (engineering) , enantioselective synthesis , asymmetric induction , medicinal chemistry , organic chemistry , stereochemistry , catalysis , medicine , materials science , alternative medicine , pathology , fermentation , metallurgy
The syntheses of optically active t ‐butyl 2‐( p ‐tolylsulfinyl)propionate and ‐butyrate ( 2a and 2b , respectively) are described, and it is shown that aldol‐type condensation of the corresponding enolates is limited by steric hindrance. Optically active (2a) reacted, however, in high yield with aliphatic aldehydes and lead to 80% of asymmetric induction.