Catalytic Asymmetric Iodocarbocyclization Reaction of 4-Alkenylmalonates and Its Application to Enantiotopic Group Selective Reaction

Tadashi Inoue, Osamu Kitagawa, Akio Saito, Takeo Taguchi

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Abstract

The iodocarbocyclization reaction of 4-alkenylmalonate derivatives proceeded with excellent enantioselectivity (≥95% ee) in the presence of 10-40 mol % of Ti(TADDOLate)2. The Ti-(TADDOLate)2-mediated catalytic asymmetric reaction was extended to the enantiotopic group selective reaction of bisalkenylated malonates, giving rise to trisubstituted cyclopentanoid compounds with both high diastereoselectivity (86-94% de) and excellent enantioselectivity (≥95% ee). An efficient synthesis of (+)-boschnialactone from the product of the present reaction was also achieved.

Original languageEnglish
Pages (from-to)7384-7389
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number21
Publication statusPublished - 1997
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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