乙烯基烯酮硅基 N,O-缩醛的远程不对称诱导作用
Remote asymmetric induction with vinylketene silyl n,o-acetal.
作者信息
Shirokawa Shin-Ichi, Kamiyama Masato, Nakamura Tomoaki, Okada Masakazu, Nakazaki Atsuo, Hosokawa Seijiro, Kobayashi Susumu
机构信息
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Nodashi, Chiba 278-8510, Japan.
出版信息
J Am Chem Soc. 2004 Oct 27;126(42):13604-5. doi: 10.1021/ja0465855.
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 alpha-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 delta-hydroxy-alpha,gamma-dimethyl-alpha,beta-unsaturated carbonyl unit that is seen in many natural polyketide products.
已经开发出一种使用手性乙烯基烯酮硅基N，O-乙缩醛的、高度区域和非对映选择性的TiCl₄介导的乙烯型Mukaiyama羟醛反应。目前的乙烯型Mukaiyama羟醛反应提供了一种控制远程不对称诱导的独特而有效的方法。α位的甲基对于实现高水平的立体选择性很重要。从合成的角度来看，这种方法可以一步构建许多天然聚酮化合物产品中可见的δ-羟基-α，γ-二甲基-α，β-不饱和羰基单元。
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