Remote Asymmetric Induction with Vinylketene Silyl N , O -Acetal
2004; American Chemical Society; Volume: 126; Issue: 42 Linguagem: Inglês
10.1021/ja0465855
ISSN1943-2984
AutoresShin-ichi Shirokawa, Masato Kamiyama, Tomoaki Nakamura, Masakazu Okada, Atsuo Nakazaki, Seijiro Hosokawa, Susumu Kobayashi,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA 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.
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