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 | Zendy

Mulzer Johann | Zendy; de Lasalle Peter | Zendy; Freißler Axel | Zendy

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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 ).

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