330652-60-3Relevant academic research and scientific papers
Enantiomerically pure cyclopropylboronic esters: Auxiliary-versus substrate-control
Pietruszka, Joerg,Witt, Andreas
, p. 4293 - 4300 (2008/10/08)
Stable, enantiomerically pure cyclopropylboronic esters are synthesized from alkynes by a hydroboration-cyclopropanation sequence. The direct hydroboration-utilizing 1,3,2-dioxaborolane 4-is most convenient, however, with more functionalized side-chains it failed to give the desired intermediates. Using the more reactive dicyclohexylborane, followed by oxidation and transesterification, is a good alternative one-pot conversion. Cyclopropanations were performed either following a Simmons-Smith protocol or with diazomethane-palladium(II) acetate. The influence on the diastereoselectivity of the auxiliary 1 is compared with the influence of an additional stereogenic center in the side-chain.
Enantiomerically pure cyclopropylboronic esters: Auxiliary- versus substrate-control
Pietruszka, Joerg,Witt, Andreas
, p. 4293 - 4300 (2007/10/03)
Stable, enantiomerically pure cyclopropylboronic esters are synthesized from alkynes by a hydroboration-cyclopropanation sequence. The direct hydroboration - utilizing 1,3,2-dioxaborolane 4 - is most convenient, however, with more functionalized side-chains it failed to give the desired intermediates. Using the more reactive dicyclohexylborane, followed by oxidation and transesterification, is a good alternative one-pot conversion. Cyclopropanations were performed either following a Simmons-Smith protocol or with diazomethane-palladium(II) acetate. The influence on the diastereoselectivity of the auxiliary 1 is compared with the influence of an additional stereogenic center in the side-chain. The Royal Society of Chemistry 2000.
