THERMAL AND LEWIS ACID-PROMOTED ASYMMETRIC HETERO-DIELS-ALDER REACTION OF A 1-THIABUTA-1,3-DIENE SYSTEM (THIOCHALCONE) WITH CHIRAL ACRYLIC ESTERS AND N-ACRYLOYL-CARBOXIMIDE AND N-CROTONYL-CARBOXIMIDE

Authors
SAITO T KARAKASA T FUJI H FURUNO E SUDA H KOBAYASHI K
Citation
T. Saito et al., THERMAL AND LEWIS ACID-PROMOTED ASYMMETRIC HETERO-DIELS-ALDER REACTION OF A 1-THIABUTA-1,3-DIENE SYSTEM (THIOCHALCONE) WITH CHIRAL ACRYLIC ESTERS AND N-ACRYLOYL-CARBOXIMIDE AND N-CROTONYL-CARBOXIMIDE, Journal of the Chemical Society. Perkin transactions. I, (11), 1994, pp. 1359-1362
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
11
Year of publication
1994
Pages
1359 - 1362
Database
ISI
SICI code
0300-922X(1994):11<1359:TALAAH>2.0.ZU;2-S
Abstract
Thermal and Lewis acid-promoted asymmetric hetero Diels-Alder reaction s of the thiabutadiene 1 with the chiral dienophiles 2-5 derived from (-)-menthol, (+)-borneol and (-)-4-benzyloxazolidinone affords the opt ically active dihydrothiopyran derivatives. The chiral induction is in the range 13-92% d.e. depending mainly upon the auxiliary chiral grou ps. The absolute configuration of the endo cycloadducts is confirmed b y the derivatization based on X-ray crystallographic analysis.