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제123회 대한화학회 학술발표회, 총회 및 기기전시회 안내 New method for homologation of ester to α,β-unsaturated esters using modified Horner–Wadsworth–Emmons (HWE) olefination

2019년 2월 14일 14시 26분 07초
ORGN.P-334 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
4월 18일 (목요일) 11:00~12:30
Organic Chemistry
저자 및
chang Whee Hong, Duk Keun An*, Hyun Tae Kim
Department of Chemistry, Kangwon National University, Korea

For the preparation of α,β-unsaturated esters, Horner–Wadsworth–Emmons (HWE) modification of the Wittig reaction is a widely used method in organic synthesis. Especially, this reaction is popular for stereoselective olefination of carbonyl compounds which are useful in the synthesis of complex natural products. Till date the HWE reaction has been extensively studied1, however most of the conditions demonstrated for aldehyde and ketone functional group. To the best of our knowledge, only few reports demonstrated with ester group.2,3 Given our interest in finding selective and one pot reactions, and the above situation was prompted us to carry out reductive-HWE reaction with ester group. Recently, we have identified reductive-HWE olifination from ester group via partial reduction followed by Wittig homologation in one pot. In continuation, the present abstract demonstrates HWE olifination with modified and efficient protocol from readily available reagents. As a result, α,β-unsaturated esters were prepared successively form the homologation of esters using LDBBA and n-BuLi under mild conditions (Scheme). 1. K. Kobayashi. et. al. Tetrahedron Letters. 2018, 59, 568-582 2. J. Jeon. et. al. Org. Lett. 2015, 17, 5792-5795. 3. J. Takacs. et. al. Tetrahedron Letters. 1986, 27, 1257-1260