Stereocontrolled Synthesis of Functionalized Bicyclic α-Methylene Butyrolactones via Tungsten-Mediated Intramolecular Allylation of Aldehydes

LH Shiu, YL Li, CL Li, CY Lao, WC Chen…

Index: Shiu, Lin-Hun; Li, Yang-Lian; Li, Chien-Le; Lao, Ching-Yu; Chen, Wei-Chen; Yu, Chin-Hui; Liu, Rai-Shung Journal of Organic Chemistry, 1999 , vol. 64, # 20 p. 7552 - 7558

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Citation Number: 9

Abstract

The syntheses of a series of CpW (CO) 2 (π-γ-lactonyl) complexes bearing a tethered aldehyde are described. These π-allyl complexes are prepared as either syn-or anti- stereoisomers. Treatment of these dicarbonyl complexes with NOBF4 and NaI in CH3CN effects an intramolecular allylation of the tethered aldehyde, yielding bicyclic α-methylene butyrolactones comprising a homoallylic alcohol. Both syn-and anti-isomers of tungsten-π- ...