The Origin of High Stereoselectivity in Di-tert-butylsilylene-directed α-Galactosylation

…, S Nakashima, H Ando, H Ishida, M Kiso

Index: Imamura, Akihiro; Ando, Hiromune; Ishida, Hideharu; Kiso, Makoto Organic Letters, 2005 , vol. 7, # 20 p. 4415 - 4418

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Abstract

The origin of the high α (1, 2-cis)-stereoselectivity in the reaction of galactosyl and galactosaminyl donors with a di-tert-butylsilylene (DTBS) group with several nucleophiles has been elucidated by means of experimental and computational approaches. DTBS overcomes any other cyclic protecting groups examined to date and the β (1, 2-trans)- directing effect due to the neighboring participation by CO groups at C2. Requirements for ...