736140-69-5Relevant articles and documents
Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O): Application of α,β-unsaturated N-Acyl pyrroles as ester surrogates
Kinoshita, Tomofumi,Okada, Shigemitsu,Park, Sun-Ryung,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 4680 - 4684 (2003)
Waste not, want not: Efficient one-pot access to optically active epoxides with 96 to 99.5% ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by-product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N-acyl pyrrole Wittig product (see scheme). The N-acyl pyrrole functionality is key to the high reactivity and selectivity observed. R = alkyl, aryl, vinyl.