서지주요정보
β-functionalization of enones via phosphoniosilylation = 포스포니오실릴레이션을 통한 α,β-불포화 케톤의 작용기화
서명 / 저자 β-functionalization of enones via phosphoniosilylation = 포스포니오실릴레이션을 통한 α,β-불포화 케톤의 작용기화 ; synthesis of β-lactams from β-amino acids using organophosohorus reagents = 유기인계 축합제를 이용한 β-아미노산으로부터 β-락탐의 합성 / Phil-Ho Lee.
저자명 Lee, Phil-Ho ; 이필호
발행사항 [서울 : 한국과학기술원, 1989].
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소장정보

등록번호

4105406

소장위치/청구기호

학술문화관(문화관) 보존서고

DAC 8910

휴대폰 전송

도서상태

이용가능

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초록정보

I. β-Functionalization of Enones via Phosphoniosilylation β-Alkoxycarbonylation, β-acylation, and β-sulfenylation of α,β-enones are achieved by the reaction of ylides, derived from enones via phosphoniosilylation, with benzyl chloroformate, benzoyl fluoride, and diphenyl disulfide, respectively, followed by the desilylation. β-Conjugate addition and β-hydroxyalkylation of α,β-enones have been accomplished by the reaction of ylides with activated olefins and aldehydes in the presence of trimethylsilyl triflate in tetrahydrofuran at -78℃ and subsequent elimination of phosphonium salts by one-pot procedure. Also, direct displacement of triphenylphosphonium salt, derived from enones via phosphoniosilylation, with several nucleophiles provides conjugate addition products in which ketone groups are protected as silylenol ethers. II. Synthesis of β-Lactams from β-Amino Acids Using Organophosphorus Reagents. Diphenylphosphinic chloride is found to be very effective condensing reagent for the formation of β-lactams from N-substituted β-amino acids. Bis(5-nitro-2-pyridyl) phenyl phosphate (NPPP) and bis(5-nitro-2-pyridyl) phenylphosphonate (BNPP) are prepared by the reaction of phenyl dichlorophosphate and phenylphosphonic dichloride, respectively, with 2-hydroxy-5-nitropyridine. NPPP and BNPP can be effectively utilized as a condensing reagent for the formation of β-lactams from N-substituted β-amino acids. Using triphenylphosphine/carbon tetrachloride system as a condensing reagent, N-substituted as well as N-unsubstituted β-amino acids are cleanly cyclized into the corresponding β-lactams in high yields under a concentrated solution.

서지기타정보

서지기타정보
청구기호 {DAC 8910
형태사항 ix, 166 p. : 삽도 ; 26 cm
언어 영어
일반주기 저자명의 한글표기 : 이필호
지도교수의 영문표기 : Sung-Gak Kim
지도교수의 한글표기 : 김성각
학위논문 학위논문(박사) - 한국과학기술원 : 화학과,
서지주기 Reference : p. 160-166
주제 Lactams.
Carbonyl compounds.
Organophosphorus compounds.
화학 합성. --과학기술용어시소러스
실릴화. --과학기술용어시소러스
락탐화. --과학기술용어시소러스
Silylation.
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