Tetrahedron Letters p. 1787 - 1790 (1995)
Update date:2022-08-03
Topics:
Saksena, Anil K.
Girijavallabhan, Viyyoor M.
Lovey, Raymond G.
Pike, Russell E.
Wang, Haiyan
et al.
A convenient synthesis of (-)-(2R)-cis-tosylate 2 is reported via stereoselective 5-exo iodocyclization of the optically active 2,2-disubstituted olefin 9a.Enzymatic desymmetrization of the homoallylic diol 4 with Novo SP435 allowed optimal pro-(S) selectivity to provide the desired (-)-(S)-monoacetate 9a.Under the irreversible reaction conditions, the presence of a bulky aryl substituent on the 2,2-disubstituted olefin seems to determine stereochemical outcome of these halocyclizations.
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