Tetrahedron Letters p. 1951 - 1954 (1997)
Update date:2022-08-05
Topics:
Mikami, Koichi
Matsukawa, Satoru
Sawa, Eiji
Harada, Akinori
Koga, Nobuaki
An anomalous nonchelation diastereofacial selectivity is observed in the titanium-catalyzed carbonyl addition reaction to benzyl-protected alkoxyaldehydes.There is a dichotomy in the sense of syn- vs. anti-diastereofacial preference, dictated by the bulkiness of the migratory group: The sterically demanding silyl group gives syn-diastereofacial preference and the less sterically demanding proton leads to anti-diastereofacial preference.
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