883884-85-3Relevant academic research and scientific papers
New enantiomerically pure allylboronic esters in allyl additions: Synthesis and NMR investigation of intermediates
Pietruszka, Joerg,Schoene, Niklas
, p. 24 - 30 (2006)
Enantiomerically pure allylboronic esters 1 + 2 with a stereogenic center α to the boron moiety can be obtained by a sigmatropic rearrangement of boron containing allyl alcohols. Allyl additions with the new reagents are highly selective, which was shown
Diastereo- and enantiomerically pure allylboronates: Their synthesis and scope
Pietruszka, Joerg,Schoene, Niklas,Frey, Wolfgang,Grundl, Li
scheme or table, 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.
