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금 촉매(I)를 이용한 N-allyl-4-yn-1-amine의 tandem 5-exo-dig 고리화

Title
금 촉매(I)를 이용한 N-allyl-4-yn-1-amine의 tandem 5-exo-dig 고리화
Authors
이미령
Date Issued
2012
Publisher
포항공과대학교
Abstract
The aza-Clsisen rearrangement is a powerful, atom-efficient method for the synthesis of functionalized amines. However, this reaction has yet been developed to be applied diversely because of the implication of harsh reaction conditions to achieve the rearrangement. Therefore, the charge-accelerated aza-Claisen rearrangements have been studied to take place under mild conditions. Furthermore, the use of transition metals such as Pd, Ru, Rh, Pt etc. has been attempted to find more efficient reaction conditions. Besides, the gold (I) catalysis has also been introduced recently as a useful strategy based on the unique characteristic of Au’s alkynophilicity. Particularly, the gold catalysts have been successfully employed to a series of [3,3]-sigmatropic rearrangements. In this thesis, the main topic is, study of highly efficient gold(I)-catalyzed tandem 5-exo-dig cyclization via aza-Claisen rearrangement reaction using an air-stable crystalline [P(C6F5)3]AuNTf2 as a catalyst. This is particularly interested towards the mechanistic aspect of this transformation, which operates via a 5-exo-dig cyclization followed by aza-Claisen rearrangement rather than fragmentation pathway. Moreover, this transformation terminated by a addition of water to produce ketones.
URI
http://postech.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000001221434
http://oasis.postech.ac.kr/handle/2014.oak/1540
Article Type
Thesis
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