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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4106-4109
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	16
DOIs	https://doi.org/10.1021/ol501805j
Publication status	Published - 2014 Aug 15

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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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T1 - Stereoselective acylation of the E, e -vinylketene silyl N, O -acetal and its application to the synthesis of khafrefungin

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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U2 - 10.1021/ol501805j

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

Abstract

ASJC Scopus subject areas

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