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An approach to homochiral fused and spiro cyclopentenones

✍ Scribed by Juan Manuel Villar; Antonio Delgado; Amadeu Llebaria; Josep M. Moretó

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 234 KB
Volume: 6
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00055-t

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✦ Synopsis

An asymmetric approach to the Ni(CO)4 induced alkyne-allyl halide cyclizationcarbonylation process by the use of homochiral acetylenic sulfoxides to afford enantiopum [5+8] fused and spiro cyclopentenones is reported.

During the last years we have been working on the synthesis of cyclopentenones by means of the Ni(CO)4 induced carbonylative inter and intrarnolecular cyclization of acetylenes with allyl halides. 1 By proper choice of the substrates, bicyclic fused and spiro cyclopentenones can be obtained in a single synthetic operation with total regio and diastereoseleefivity. 2 As an extension of our efforts in this field we wish to report on the development of an asymmetric approach to this process making use of homochiral acetylenic sulfuxides as chiral auxiliaries to obtain enantiopure [5+8] fused and spiro systems (Scheme 1).

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