有機不對稱連鎖反應：以1,3-共軛烯炔與烯胺酮衍生物進行Michael/oxa-Michael加成反應建立四氫-4H-苯併吡喃架構
No Thumbnail Available
Date
2017
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
以有機催化劑進行有機不對稱連鎖反應進行，建構高鏡像選擇性之四氫-4H-苯並吡喃架構之產物。使用1,3-硝基共軛烯炔及烯胺酮，以氯仿為溶劑並利用20%之奎寧-硫尿素衍生之雙關能基催化劑，透過催化劑上三級胺及硫尿素之氫鍵催化，於0 oC，下進行兩分子間[3+3]合環反應，經由Michael/丙二烯生成/oxa-Micheal之過程得到四氫-4H-苯並吡喃架構為主架構之產物，最高可達48%產率，以及不錯的鏡像選擇性(up to >99%)。
The method is to construct high enatioseletivity of fourhydro-4H-chromene scaffold via bifunctional organocatalyst. The organocascade reaction is carried out between 1,3-nitro enynes and enaminones to afford tetrahydro-4H-chromene structures in CHCl3 through hydron-bonding interaction under 0 degree. The reaction proceeds through sequential conjugate Michael addition/allene formation/intramolecular oxa-Michael addition in medium yield (up to 48% yield) and excellent stereoselectivites (up to >99%).
The method is to construct high enatioseletivity of fourhydro-4H-chromene scaffold via bifunctional organocatalyst. The organocascade reaction is carried out between 1,3-nitro enynes and enaminones to afford tetrahydro-4H-chromene structures in CHCl3 through hydron-bonding interaction under 0 degree. The reaction proceeds through sequential conjugate Michael addition/allene formation/intramolecular oxa-Michael addition in medium yield (up to 48% yield) and excellent stereoselectivites (up to >99%).
Description
Keywords
有機連鎖反應, [3+3]合環反應, 1, 3-共軛烯炔, Organocascaed, [3+3]-cycloaddtion, 1, 3-enyne