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Diastereoselective Synthesis of Useful Building Blocks by Crotylation of Beta-Branched Alpha-Methylaldehydes With Potassium Crotyltrifluoroborates

Kyosuke Tanaka, Yukiko Fujimori, Yoko Saikawa, Masaya Nakata

J Org Chem. 2008 Aug 15;73(16):6292-8.

PMID: 18630883

Abstract:

The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium ( E)-crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP329976796 Potassium octyltrifluoroborate Potassium octyltrifluoroborate 329976-79-6 Price
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