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- and N-crotonyl-carboximides

Autor:	Takayuki Karakasa, Eiji Furuno, Hiroya Fujii, Hirofumi Suda, Takao Saito, Kimiko Kobayashi
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Acid catalysis Chiral auxiliary chemistry Diene Absolute configuration Organic chemistry Lewis acids and bases Derivatization Medicinal chemistry Chiral induction Diels–Alder reaction
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1359-1362
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19940001359
Popis:	Thermal and Lewis acid-promoted asymmetric hetero Diels–Alder reactions of the thiabutadiene 1 with the chiral dienophiles 2–5 derived from (–)-menthol, (+)-borneol and (–)-4-benzyloxazolidinone affords the optically active dihydrothiopyran derivatives. The chiral induction is in the range 13–92% d.e. depending mainly upon the auxiliary chiral groups. The absolute configuration of the endo cycloadducts is confirmed by the derivatization based on X-ray crystallographic analysis.
Databáze:	OpenAIRE
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