1,4-addition of chiral 2-propenylphosphonamide anions to alpha-substitutedcyclopentenones: use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates

Authors
Hailes, HC Isaac, B Javaid, MH
Citation
Hc. Hailes et al., 1,4-addition of chiral 2-propenylphosphonamide anions to alpha-substitutedcyclopentenones: use in enantioselective syntheses of methyl dihydrojasmonates and methyl jasmonates, TETRAHEDR L, 42(41), 2001, pp. 7325-7328
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
41
Year of publication
2001
Pages
7325 - 7328
Database
ISI
SICI code
0040-4039(20011008)42:41<7325:1OC2AT>2.0.ZU;2-E
Abstract
The addition of chiral 2-propenylphosphonamide anions, generated from the r eaction products of (1R,2S)-ephedrine and 2-propene-1-phosphonyl dichloride , to alpha -substituted cyclopentenones is described. Ozonolysis of the add ition products led to the synthesis of both enantiomers of methyl dihydroja smonate and methyl jasmonate. (C) 2001 Elsevier Science Ltd. All rights res erved.