Studies on the functionalization of α,β-unsaturated carbonyl compounds = 알파,베타-불포화 카르보닐 화합물들의 작용기화에 관한 연구

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Sulfoniosilylation of $\alpha,\,\beta$ -unsaturated carbonyl compounds with dimethyl sulfide and trialkylsilyl triflate at -70$^\circ$C yields $\beta$ -dimethylsulfonium silyl enol ethers which is stable at low temperature but decomposed as the temperature is raised to room temperature. $\beta$ -Functionalization of $\alpha,\,\beta$ -unsaturated ketones could be successfully carried out by the reaction of $\beta$ -dimethylsulfonium silyl enol ethers with various nucleophiles such as lithium thiolates, lithium enolate of esters, and enamines. Furthermore, $\beta$ -dimethylsulfonium alkyl enol ethers derived from $\alpha,\,\beta$ -unsaturated aldehyde dialkyl acetals gave $\alpha,\,\beta$ -enal monothioacetals in good yields by reacting with lithium thiolates in tetrahydrofuran at -78$^\circ$C. $\alpha$ -Alkoxyalkylation of $\alpha,\,\beta$ -unsaturated ketones could be carried out by the reaction of $\beta$ -dimethylsulfonium silyl enol ethers with acetals, followed by elimination of dimethyl sulfide by using DBU. TBSOTf promoted conjugate addition of organometallic reagents such as alkynylzinc bromides, diethylzinc, Reformatsky reagents, and allyltins to $\alpha,\,\beta$ -enones.
Advisors
Kim, Sung-Gakresearcher김성각researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1991
Identifier
61608/325007 / 000865339
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1991.2, [ v, 123 p. ]

URI
http://hdl.handle.net/10203/31345
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=61608&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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