1044871-05-7Relevant academic research and scientific papers
Enantioselective Catalysts for the Synthesis of α-Substituted Allylboronates - An Accelerated Approach towards Isomerically Pure Homoallylic Alcohols
Brauns, Marcus,Muller, Frdric,Gülden, Daniel,B?se, Dietrich,Frey, Wolfgang,Breugst, Martin,Pietruszka, J?rg
, p. 1548 - 1552 (2016)
The use of a convenient protecting group for boronates allows a selective, catalyzed SN2′ reaction to generate allylboronates which are applied for the synthesis of enantiomerically pure homoallylic alcohols. Depending on the configuration of both catalyst and the protecting group any of the four possible stereoisomers can be formed. The rationale behind the selective addition is supported by density functional theory calculations.
Diastereo- and enantiomerically pure allylboronates: Their synthesis and scope
Pietruszka, Joerg,Schoene, Niklas,Frey, Wolfgang,Grundl, Li
experimental part, p. 5178 - 5197 (2009/07/18)
Allylboronates are highly attractive reagents for allyl additions. Enantiomerically pure, stable reagents with a stereogenic centre in a-position to boron are especially versatile, albeit often difficult to synthesize. Starting from boron-containing allyl alcohols 6 and 7, which are discussed in detail herein, a set of reagents were obtained via [3,3]-sigmatropic rearrangements and consecutive transformations in the side chain. The configurations could be established first by chemical correlation, but also by X-ray crystallography (16, 18, 34, and 39). Allyl additions were performed resulting in the formation of predominantly (Z)-configured homoallylic alcohols (31, 43-45) with high enantiomeric excess. Detailed investigations on the matched-mismatched interaction between the reagents 15/16 (and ent-15/ent-16, respectively) and isopropylidene glyceraldehyde 42 d are presented.
