Cyclofunctionalisation of epoxyalcohol derivatives. 1. Delivery of functionalised carbon for stereospecific synthesis of dihydrofurans and dihydroxyacids

✍ Scribed by Stuart W. McCombie; Bandarpalle B. Shankar; Ashit K. Ganguly

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 194 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)84583-4

✦ Synopsis

Reaction of a 2,3-epoxyalcohol (3) with E-chlorovinyl phenyl sulfone (4)l" or E-l ,2-bis-(phenylsulfonyl)ethene (5)L1 CNaH-THFI produced ether (6), reagent (5) being preferred for maximum yields. Upon generation of the vinylsulfonyl carbanion l2 KLDA.

-70'1 followed by warming to O", cyclisation with C-2 inversion occurred to give the dihydrofuran (7). Table 1 shows results for some representative 2,3-epoxyalcohols. The 3,4-epoxyalcohol (8) was similarly converted to (9).