Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

Naoya Sagawa; Haruka Sato; Seijiro Hosokawa

doi:10.1021/acs.orglett.6b03476

Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

Naoya Sagawa, Haruka Sato, Seijiro Hosokawa^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

17 被引用数 (Scopus)

抄録

Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl₄ and BF₃·OEt₂, respectively. The SnCl₄-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.

本文言語	English
ページ（範囲）	198-201
ページ数	4
ジャーナル	Organic Letters
巻	19
号	1
DOI	https://doi.org/10.1021/acs.orglett.6b03476
出版ステータス	Published - 2017 1月 6

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/acs.orglett.6b03476

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title = "Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals",

abstract = "Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.",

author = "Naoya Sagawa and Haruka Sato and Seijiro Hosokawa",

note = "Funding Information: We are grateful for financial support from The Kurata Memorial Hitachi Science and Technology Foundation and The Naito Foundation. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.orglett.6b03476",

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T1 - Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

AU - Sagawa, Naoya

AU - Sato, Haruka

AU - Hosokawa, Seijiro

N1 - Funding Information: We are grateful for financial support from The Kurata Memorial Hitachi Science and Technology Foundation and The Naito Foundation. Publisher Copyright: © 2016 American Chemical Society.

PY - 2017/1/6

Y1 - 2017/1/6

N2 - Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.

AB - Remote asymmetric induction by the vinylogous Mukaiyama aldol reaction using the acetate-type vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved. The silyl N,O-acetal derived from crotonate and L-valine afforded the O-silylated 5R- and 5S-adducts selectively by treatment with SnCl4 and BF3·OEt2, respectively. The SnCl4-mediated isomerization of silyl dienol ether was found, and the resulting major isomer showed high reactivity to give γ-adduct in high stereoselectivity.

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Remote asymmetric induction using acetate-type vinylketene silyl N,O-acetals

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