Remote asymmetric induction with vinylketene silyl N,O-acetal

Shin Ichi Shirokawa, Masato Kamiyama, Tomoaki Nakamura, Masakazu Okada, Atsuo Nakazaki, Seijiro Hosokawa, Susumu Kobayashi

Research output: Contribution to journalArticle

142 Citations (Scopus)

Abstract

A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of controlling remote asymmetric induction. The methyl group at the α-position is important in achieving a high level of stereoselectivity. From a synthetic point of view, this methodology can provide a one-step construction of δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl unit that is seen in many natural polyketide products.

Original languageEnglish
Pages (from-to)13604-13605
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number42
DOIs
Publication statusPublished - 2004 Oct 27
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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  • Cite this

    Shirokawa, S. I., Kamiyama, M., Nakamura, T., Okada, M., Nakazaki, A., Hosokawa, S., & Kobayashi, S. (2004). Remote asymmetric induction with vinylketene silyl N,O-acetal. Journal of the American Chemical Society, 126(42), 13604-13605. https://doi.org/10.1021/ja0465855