Tandem [4+2]/[3+2]-cycloadditions. 2. Asymmetric induction with a chiral vinyl ether

Scott E. Denmark, C. B.W. Senanayake, Ho Ginny-Dai

Research output: Contribution to journalArticle

Abstract

A tandem [4+2]/[3+2]-cycloaddition of nitroalkenes tethered to α,β-unsaturated ester dipolarophiles can be effectively triggered with a vinyl ether. Using the chiral vinyl ether 6 as the dienophile, nitroalkenes 1 and 2 undergo highly selective tandem cycloaddition. Hydrogenolytic cleavage of the resulting nitroso acetals produce α-hydroxy lactams (-)-14 and (-)-21 in >98% e.e. with excellent recovery of the chiral auxiliary. The high diastereoselectivity is seen to arise from a strong endo preference for the vinyl ether together with an intrinsic facial bias in the auxiliary.

Original languageEnglish (US)
Pages (from-to)4857-4876
Number of pages20
JournalTetrahedron
Volume46
Issue number13-14
DOIs
StatePublished - 1990

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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