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Addition of crotylchromium(II) and dilithium propionate to ( R )‐2,3‐ O ‐isopropylideneglyceraldehyde: Steric course and synthetic application in a formal synthesis of (+)‐ and (−)‐δ‐multistriatin
Author(s) -
Mulzer Johann,
de Lasalle Peter,
Freißler Axel
Publication year - 1986
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198619860704
Subject(s) - dilithium , chemistry , propionate , steric effects , enantiomer , adduct , bromide , formal synthesis , selectivity , stereochemistry , salt (chemistry) , medicinal chemistry , organic chemistry , catalysis , ion , deprotonation
The chromium(II) salt 4a of crotyl bromide adds to ( R )‐2,3‐ O ‐isopropylideneglyceraldehyde ( 1 ) with high enantiofacial and low diastereofacial ( i. e. Cram) selectivity, whereas dilithium propionate ( 9 ) shows the opposite behaviour. The adducts 5, 7 , and 10 can be used in a formal synthesis of both enantiomers of the insect pheromone δ‐multistriatin ( 30 ).