Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin

Yuta Takahashi; Maiko Otsuka; Mio Harachi; Yuki Mukaeda; Seijiro Hosokawa

doi:10.1021/ol501805j

Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin

Yuta Takahashi, Maiko Otsuka, Mio Harachi, Yuki Mukaeda, 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

19 被引用数 (Scopus)

抄録

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl₄. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

本文言語	English
ページ（範囲）	4106-4109
ページ数	4
ジャーナル	Organic Letters
巻	16
号	16
DOI	https://doi.org/10.1021/ol501805j
出版ステータス	Published - 2014 8月 15

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/ol501805j

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abstract = "Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.",

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AU - Takahashi, Yuta

AU - Otsuka, Maiko

AU - Harachi, Mio

AU - Mukaeda, Yuki

AU - Hosokawa, Seijiro

PY - 2014/8/15

Y1 - 2014/8/15

N2 - Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

AB - Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

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Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin

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