TY - JOUR
T1 - Remote asymmetric induction with vinylketene silyl N,O-acetal
AU - Shirokawa, Shin Ichi
AU - Kamiyama, Masato
AU - Nakamura, Tomoaki
AU - Okada, Masakazu
AU - Nakazaki, Atsuo
AU - Hosokawa, Seijiro
AU - Kobayashi, Susumu
PY - 2004/10/27
Y1 - 2004/10/27
N2 - 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 α-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 δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl unit that is seen in many natural polyketide products.
AB - 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 α-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 δ-hydroxy-α,γ-dimethyl-α,β-unsaturated carbonyl unit that is seen in many natural polyketide products.
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U2 - 10.1021/ja0465855
DO - 10.1021/ja0465855
M3 - Article
C2 - 15493903
AN - SCOPUS:6444223032
SN - 0002-7863
VL - 126
SP - 13604
EP - 13605
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 42
ER -