125950-71-2Relevant academic research and scientific papers
Enzymatic kinetic resolution of α-hydroxysilanes
An, Ilhwan,Onyeozili, Edith N.,Maleczka Jr., Robert E.
experimental part, p. 527 - 534 (2010/08/22)
The enzymatic kinetic resolution of α-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various α-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active α-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees.
Stereoselective Nucleophilic Additions to Trialkylsilyl-Substituted Acyclic Acetals
Linderman, Russell J.,Anklekar, Tarakeshwar V.
, p. 5078 - 5080 (2007/10/02)
Regioselective and diastereoselective Mukaiyama-type aldol reactions of silyl-substituted mixed acyclic acetals provide the aldol products with 5:1 to 14:1 selectivity.
The Synthesis of α-Stannyl Silanes and Their Use in the Formation of Alkenes
Barrett, Anthony G. M.,Hill, Jason M.
, p. 3285 - 3288 (2007/10/02)
α-Stannyl-silanes were prepared from aldehydes via α-hydroxy- and α-chloro-silanes.Stannyl-silane 5d was transmetallated using n-butyllithium and the resultant α-lithio-silane condensed with aldehydes to yield alkenes.
Synthetic utility and mechanistic studies of the aliphatic reverse brook rearrangement
Linderman, Russell J.,Ghannam, Ameen
, p. 2392 - 2398 (2007/10/02)
The aliphatic reverse Brook rearrangement has been examined in detail. Transmetalation of [α-[(trialkylsilyl)-oxy]alkyl]trialkylstannanes occurs via a complex equilibrium favoring the most stable carbanion. The aliphatic reverse Brook rearrangement is driven forward by the rapid migration of silicon from O to C in a transient α-silyloxy carbanion due to the formation of the more stable lithium alkoxide. Cross-over experiments have shown that the rearrangement is an intramolecular process while incorporation of a radical trap revealed that the rearrangement does not involve radical intermediates. Studies of configurationally fixed stannanes derived from 4-tert-butylcyclohexanone concluded that the rearrangement occurs with retention of configuration. Preparation and reverse Brook rearrangement of optically active (S)-[α-[(trimethylsilyl)oxy]-hexyl]tributylstannane (98% ee) provided 1-(trimethylsilyl)hexanol in 97% ee. The synthetic utility of this method for the preparation of a variety of (α-hydroxyalkyl)trialkylsilanes from aldehydes has also been demonstrated.
