title: Efficient asymmetric synthesis of silanediol precursors from 1,5-dihydrosiloles.
abstract: 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.
authors.affiliation: Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, USA.
authors.forename: Sushmita
authors.initials: S
authors.lastname: Sen
authors.forename: Madhusudhan
authors.initials: M
authors.lastname: Purushotham
authors.forename: Yingmei
authors.initials: Y
authors.lastname: Qi
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth
mesh_terms: D000466:Alkadienes / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D012821:Silanes; C475536:silanediol