103108-36-7Relevant academic research and scientific papers
Supersilylating agents from chlorosilanes
Davis, Anthony P.,Muir, Jayne E.,Plunkett, Stephen J.
, p. 9401 - 9402 (1996)
The addition of R3SiCl to B(OTf)3 gives 'supersilylating agents' formulated as R3SiB(OTf)3Cl. The catalytic properties of these species are similar to those of the previously-described (but less accessible) Rsu
Reagent Control of Cram-type Selectivity in the Mukaiyama Aldol Catalysed by Supersilylating Agents
Davis, Anthony P.,Plunkett, Stephen J.
, p. 2173 - 2174 (2007/10/02)
In the addition of silyl enol ethers 8 to α-asymmetric aldehydes 1 and 2, catalysed by 'supersilylating agents' R3SiB(OTf)4, the level of Cram-type selectivity correlates with the steric bulk of the silyl group; use of the triisopropylsilyl enol ether 8d results in unprecedented levels of 1,2-asymmetric induction.
DIASTEREOFACIAL SELECTIVITY VIA ALDOL REACTIONS USING ETHYL DITHIOACETATE AND ETHYL DITHIOPROPIONATE ENOLATES
Meyers, A. I.,Walkup, Robert D.
, p. 5089 - 5106 (2007/10/02)
The lithium enolate of ethyl dithioacetate reacts with α-methyl aldehydes to yield the aldol products in which the syn configuration in the positions β and γ to the thiocarbonyl of the product is favored over the anti configuration.This selectivity is solvent-dependent, and is enhanced at lower temperatures.In most cases, syn:anti product ratios obtained under these conditions varied from 57:43 to >99:1, depending upon the structure of the α-methyl aldehyde.When the lithium enolate of ethyl dithiopropionate was allowed to react with α-methyl aldehydes, only two out of the four possible diastereomers were detected in the product mixtures.
