Alkylidenesilacyclopropanes derived from allenes: applications to the selective synthesis of triols and homoallylic alcohols.
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.
Buchner
Kay M
KM
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Clark
Timothy B
TB
Loy
Janice M N
JM
Nguyen
Thong X
TX
Woerpel
K A
KA
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
D000438:Alcohols; D000466:Alkadienes; D003521:Cyclopropanes; D012821:Silanes; C025947:propadiene