Stereocontrolled synthetic routes to various syn-β-amino alcohol derivatives = 다양한 신-베타-아미노 알콜 유도체들의 입체선택적인 합성법들

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Stereocontrolled synthetic routes to various syn-β-amino alcohol derivatives were accomplished. Bis(trichloroacetimidate) prepared in situ from 3-buten- 1,2-diol was subjected to iodocyclization to yield dihydro-1,3-oxazine cis-44e with 93% diastereomeric excess, which was transformed into a variety of syn-b- amino alcohols 154a-f via aziridine 153. Efficient syntheses of statine and its analogues were attained from aziridine diols R-149 and S-149, which were prepared via iodocyclization of trichloroacetimidates of chiral 3-buten-1,2-diols R-136 and S-136. Olefinic diols 190 and 203 were iodocyclized to provide dihydro-1,3-oxazine 196a and oxazolidine 206a with 90 and 93% de, respectively, which were served as the precursors of various $C_2$ symmetric and meso-amino alcohols. $C_2$ Symmetric and meso-iodo hydroxy ammonium chlorides generated from 196a and 206a were cyclized under basic conditions to produce various heterocycles chemoselectively, which comprise tetrahydrofurans 214 and 228, piperidines 220, 222 and 230, and pyrrolidines 224 and 225. For the synthesis of a key intermediate to 1β-methylcarbapenem antibiotics, aziridine 233 was prepared from alcohol 234 via iodoamination. Regioselective opening reaction of 233 with cyanide provided 255a, which has the requisite four contiguous chiral centers. But conversion of nitrile 255a into azetidinone carboxylic acid 155 was not achieved.
Advisors
Kang, Sung-Horesearcher강성호researcher
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
1997
Identifier
112609/325007 / 000935119
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 1997.2, [ iii, 165 p. ]

Keywords

Iodocyclization; Syn-$\beta$ -amino alcohol; Aziridine; 아지리딘; 요오드화 고리반응; 신-베타-아미노 알콜

URI
http://hdl.handle.net/10203/31455
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=112609&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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