Synthesis of Oxygen Containing Cyclic Compounds from a Chiral Aziridine
- 주제(키워드) aziridine
- 발행기관 서강대학교 일반대학원
- 지도교수 이원구
- 발행년도 2010
- 학위수여년월 2010. 2
- 학위명 석사
- 학과 일반대학원 바이오융합기술협동과정
- 실제URI http://www.dcollection.net/handler/sogang/000000045833
- 본문언어 영어
- 저작권 서강대학교의 논문은 저작권에 의해 보호받습니다
초록/요약
Abstract Synthesis of Oxygen Containing Cyclic Compounds from a Chiral Aziridine 5-Membered ring (1,3-dihydroisobenzofuran derivatives) Various enantiomerically pure 2-acylaziridines were prepared efficiently from the corresponding aziridine-2-carboxylate via Weinreb？s amide and the subsequent treatment of o-halostyrene and n-BuLi. The carbonyl group of those 2-acylaziridines was stereoselectively reduced to give 1,2-amino alcohols with high diastereoselectivities and chemical yields. The olefin of the styrene was ozonolized and reduced by NaBH4 to give the corresponding benzyl alcohol derivatives. Then 1,3-dihydroisobenzofuran was synthesized via intramolecular cyclization of the diols of enantiomerically pure aziridine-2-methanols. 6-Membered ring (Isochroman derivatives) Various enantiomerically pure 2-acylaziridines were prepared efficiently from the corresponding aziridine-2-carboxylate via Weinreb？s amide and the subsequent treatment of TBS protected 2-bromo phenethyl alcohol and n-BuLi. The carbonyl group of those 2-acylaziridines was stereoselectively reduced to give 1,2-amino alcohols with high diastereoselectivities and chemical yields. Then isochroman derivative was synthesized via nucleophilic displacement of the ？OTs between diols. 7-Membered ring (1,3,4,5-tetrahydrobenzo[c]oxepine derivatives) Various enantiomerically pure 2-acylaziridines were prepared efficiently from the corresponding aziridine-2-carboxylate via Weinreb？s amide and the subsequent treatment of o-halostyrene and n-BuLi. The carbonyl group of those 2-acylaziridines was stereoselectively reduced to give 1,2-amino alcohols with high diastereoselectivities and chemical yields. The 2-amino alcohol was allylated with allyl bromide to give the corresponding allyl ether derivatives. Then, 1,3,4,5-tetrahydrobenzo[c]oxepine was synthesized via Ring Closing Metathesis using Grubbs (II) catalyst.
more초록/요약
요약 광학활성을 가진 아지리딘으로부터 산소를 포함한 고리구조 화합물을 효율적으로 합성하였다. 산소를 포함한 5각 고리구조 화합물 (1,3-dihydroisobenzofuran derivatives) Aziridine-2-carboxylate와 o-halostyrene 의 반응으로부터 합성된 광학적으로 순수한2-acylaziridines을 선택적으로 reduction시켜 1,2-amino alcohol을 얻는다. 이 화합물 내의 olefin으로부터 ozonolysis 와 reduction을 통해 benzyl alcohol derivative을 도입한 후, aziridine-2-methanols 의 diol 간 분자 내 고리화 반응으로 1,3-dihydroisobenzofuran derivatives 를 성공적으로 합성할 수 있다. 산소를 포함한 6각 고리구조 화합물 (Isochroman derivatives) Aziridine-2-carboxylate 와TBS protected 2-bromo phenethyl alcohol 의 반응으로부터 합성된 광학적으로 순수한2-acylaziridines을 선택적으로 reduction시켜 1,2-amino alcohol을 얻는다. 선택적으로 tosylation된 primary alcohol 과 secondary alcohol 사이의 분자 내 고리화 반응으로 isochroman derivatives 를 성공적으로 합성할 수 있다. 산소를 포함한 7각 고리구조 화합물 (1,3,4,5-tetrahydrobenzo[c]oxepine derivatives) Aziridine-2-carboxylate와 o-halostyrene의 반응으로부터 합성된 광학적으로 순수한2-acylaziridines을 선택적으로 reduction시켜 1,2-amino alcohol을 얻는다. 이 화합물 내의 alcohol을 allylation 시켜 allyl ether유도체를 합성한 후, Grubbs (II) 촉매를 사용하여 분자 내 olefin 간의 Ring Closing Metathesis 반응으로 1,3,4,5-tetrahydrobenzo[c]oxepine derivatives 를 성공적으로 합성할 수 있다.
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