title: Alkylidenesilacyclopropanes derived from allenes: applications to the selective synthesis of triols and homoallylic alcohols.
abstract: Several alkylidenesilacyclopropanes were prepared by silver-mediated silylene transfer to allenes. Oxasilacyclopentanes derived from allenes were prepared with high regio- and diastereoselectivity by a two-step, one-flask silacyclopropanation/carbonyl insertion reaction. Triols and homoallylic alcohols were formed diastereoselectively by functionalizing the oxasilacyclopentanes. An optically active allene (>98% ee) was utilized to synthesize an enantiopure homoallylic alcohol in 96% ee.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
authors.forename: Kay M
authors.initials: KM
authors.lastname: Buchner
authors.forename: Timothy B
authors.initials: TB
authors.lastname: Clark
authors.forename: Janice M N
authors.initials: JM
authors.lastname: Loy
authors.forename: Thong X
authors.initials: TX
authors.lastname: Nguyen
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000466:Alkadienes; D003521:Cyclopropanes; D012821:Silanes; C025947:propadiene