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  • 02월 26일 17시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제115회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Part 1. A Catalytic Enantioselective Glycolate Aldol Reaction via Lewis Base Activation of Lewis Acids
Part 2. A General Enantioselective Approach to the Chemical Synthesis of the Chlorosulfolipids

2015년 2월 25일 15시 52분 59초
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목 09시 : 00분
유기화학 - Current Trends in Organic Chemistry I: Catalytic Organic Reactions
저자 및
GIST 화학과, Korea
Part 1. A general, efficient, Lewis-base catalyzed enantioselective addition of glycolate-derived silyl ketene acetals to a wide range of aldehydes will be presented. Both syn- and anti-diastereomers are accessible without changing the catalyst or controlling the geometry of the silyl ketene acetal. Simple modification of the size of alkyl groups on the silyl ketene acetal is sufficient to reverse the stereochemical course of the addition. The observed diastereoselectivity and reactivity could be rationalized by the analysis of six open transition state structures with the aid of computational analysis.

Part 2. A concise and general approach has been developed for the enantioselective synthesis of three structurally related chlorosulfolipids. Key advances include highly stereocontrolled additions to a,b-dichloroaldehydes, kinetic resolution of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metathesis of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and eleven steps, respectively.

1. Chung, W.-j.; Carlson, J. S.; Vanderwal, C. D. J. Org. Chem. 2014, 79, 2226-2241.
2. Chung, W.-j.; Vanderwal, C. D. Acc. Chem. Res. 2014, 47, 718-728.
3. Chung, W.-j.; Carlson, J. S.; Bedke, D. K.; Vanderwal, C. D. Angew. Chem. Int. Ed. 2013, 52, 10052-10055.
4. Denmark, S. E.; Chung, W.-j. J. Org. Chem. 2008, 73, 4582-4595.
5. Denmark, S. E.; Chung, W.-j. Angew. Chem. Int. Ed. 2008, 47, 1890-1892.