Journal of the American Chemical Society p. 527 - 532 (1987)
Update date:2022-08-04
Topics:
Harada, Toshiro
Hayashiya, Toshio
Wada, Isao
Iwa-ake, Naoko
Oku, Akira
The enantioselective functionalization of a prochiral hydroxyl group in 2-substituted 1,3-propanediols (HOCH2CR1R2CH2OH) is presented.The reaction of the bis(trimethylsilyl) derivative of the diol with l-menthone in the presence of trimethylsilyl trifluoromethanesulfonate selectively gave one of the diastereomers of the spiroketal in which the larger substituent (R1) occupies an equatorial position.The equatorial spiroketal was treated with acetophenone enol trimethylsilyl ether in the presence of titanium tetrachloride to give the ring-cleavage product
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Doi:10.1002/adsc.200700171
(2007)Doi:10.1016/j.bmcl.2008.06.061
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(1986)Doi:10.1016/S0040-4020(01)87362-2
(1986)Doi:10.1016/S0040-4039(00)91098-0
(1975)Doi:10.1021/ja00237a032
(1987)