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제124회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Asymmetric Methallylation and Allylation Reactions with Silane Compounds Catalyzed by a Chiral Lewis Acid

2019년 8월 29일 14시 16분 19초
ORGN.P-439 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 18일 (금요일) 11:00~12:30
Organic Chemistry
저자 및
Taehyeong Kim, Hye Min Jeong1, Do Hyun Ryu*
Department of Chemistry, Sungkyunkwan University, Korea
1Sungkyunkwan University, Korea
The asymmetric methallylation and allylation of aldehydes are one of the carbon–carbon bond-forming reactions in chemical synthesis and have been regarded as a testing ground for new asymmetric methodology. Enantiomerically pure homoallylic alcohols are common synthetic intermediates. The enantioselective methallylation of aldehydes is also important asymmetric transformations in organic synthesis, but rather less developed. Homoallylic alcohols are typically generated by allylmetal-aldehyde addition reactions. A novel strategy has been developed for an enantioselective methallylation and allylation reaction of aromatic and aliphatic aldehydes with silane compounds catalyzed by a chiral Lewis acid. Silane compounds possess high thermal stability, nontoxicity, and rather low sensitivity to moisture and oxygen. In the end, the reaction provides homoallylic alcohols in good yields and with high enantioselectivity. This reaction shows promising utility in various other challenging chemical reactions and conspicuous biological activity. [References] Kaib, P. S. J.; Schreyer, L.; Lee, S.; Properzi, R.; List, B. Angew. Chem. Int. Ed. 2016, 55 , 13200-13203. Mahlau, M.; Garcia-Garcia, P.; List, B. Chem. Eur. J. 2012, 18 , 16283-16287 Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron : Asymmetry., 2003, 14 , 1603-1605