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Efficient Asymmetric Synthesis of Silanediol Precursors from 1,5-Dihydrosiloles

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journal contribution
posted on 22.11.2007, 00:00 by Sushmita Sen, Madhusudhan Purushotham, Yingmei Qi, Scott McN. Sieburth
Dihydrosiloles are easily prepared from 1,3-dienes and dichlorosilanes, even on kilogram scale. Asymmetric hydroboration of a 3-alkyl-1,5-dihydrosilole, prepared from a 2-alkyl-1,3-diene, followed by treatment with aqueous HF results in Peterson fragmentation, forming optically active 3-alkyl-4-fluorosilyl-1-butenes. The fluorosilanes are stable to moisture but very reactive toward nucleophiles. In addition, they can be converted to nucleophilic silyllithium reagents.