Remote Asymmetric Induction Using Acetate-Type Vinylketene Silyl N,O-Acetals

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• 作者：Naoya Sagawa ; Haruka Sato ; Seijiro Hosokawa
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：198-201
• 全文大小：389K
• ISSN：1523-7052

文摘

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.