Tetrahedron

Polarized ketene dithioacetals 63: Stereoselective synthesis of α-ylidene-γ-butyrolactones11Part 62; A. Datta, H. Ila and H. Junjappa, Synthesis (submitted).

A Datta, H Ila, H Junjappa

Index: Datta, Apurba; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar Tetrahedron, 1987 , vol. 43, # 22 p. 5367 - 5374

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Citation Number: 12

Abstract

A facile method for highly stereoselective synthesis of α-arylidene (4a–4d, 4f–4h and 4j) and α-ethylidene (4e, 4i)-γ-butyrolactones has been developed by acid catalyzed lactonization of the corresponding α-ylidene-γ, δ-unsaturated esters 3a–3j. The required esters 3a–3i were obtained by regioselective reduction of the corresponding α-oxo-α-allyl (or substituted allyl) ketene dithioacetals 1a–1j with sodium borohydride and subsequent boron-trifluoride ...