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

138 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

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Stereoselectivity
Acetals
Polyketides
3-hydroxybutanal
titanium tetrachloride

ASJC Scopus subject areas

  • Chemistry(all)

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

Remote asymmetric induction with vinylketene silyl N,O-acetal. / Shirokawa, Shin Ichi; Kamiyama, Masato; Nakamura, Tomoaki; Okada, Masakazu; Nakazaki, Atsuo; Hosokawa, Seijiro; Kobayashi, Susumu.

In: Journal of the American Chemical Society, Vol. 126, No. 42, 27.10.2004, p. 13604-13605.

Research output: Contribution to journalArticle

Shirokawa, SI, 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, vol. 126, no. 42, pp. 13604-13605. https://doi.org/10.1021/ja0465855
Shirokawa SI, Kamiyama M, Nakamura T, Okada M, Nakazaki A, Hosokawa S et al. Remote asymmetric induction with vinylketene silyl N,O-acetal. Journal of the American Chemical Society. 2004 Oct 27;126(42):13604-13605. https://doi.org/10.1021/ja0465855
Shirokawa, Shin Ichi ; Kamiyama, Masato ; Nakamura, Tomoaki ; Okada, Masakazu ; Nakazaki, Atsuo ; Hosokawa, Seijiro ; Kobayashi, Susumu. / Remote asymmetric induction with vinylketene silyl N,O-acetal. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 42. pp. 13604-13605.
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