利用鐵和金輔佐含氮五員、七員、九員環化合物的生成

No Thumbnail Available

Date

2012

Journal Title

Journal ISSN

Volume Title

Publisher

Abstract

本論文共分成兩個部分: 第一部份: 金(I)離子催化8-苯基-5-N-2,3-環氧基-5-甲苯磺醯基-7-炔-1-醇得到(Z)-4-苯基-7-甲苯磺醯基-3,10-二氧-7-氮雙環[7.1.0]癸-4-烯化合物。以三氟甲磺酸與此含氮醚類九員環環氧化物反應得到7-苯基-4-甲苯磺醯基-8,10-二氧-4-氮雙環[5.2.1]-2-癸基三氟甲磺酸。當金(I)離子催化取代基為間位硝基苯或間位酯基苯時,得到(Z)-4-苯亞甲基-6-甲苯磺醯基-3,9-二氧-6-氮雙環[6.1.0]壬烷化合物。 第二部分: N-((2-羥甲基)環丙基)甲基)-4-甲基-N-(3-苯基丙-2-炔基)苯磺醯胺以鐵(III)進行環化反應得到(Z)-3-(氯(苯基)亞甲基)-4-環丙基-1-甲苯磺醯基吡咯啶。若反應物為二級醇衍生物則生成具有單一選擇性的(Z)-5-(氯(苯基)亞甲基)-6-甲基-3-苯磺醯胺-3-氮雙環[5.1.0]辛烷化合物。
The thesis is divided into two parts: Part 1: Gold(I)-catalyzed 8-phenyl-5-aza-2,3-epoxy-5-tosyl-7-yn-1-ol afforded (Z)-4-phenyl-7-tosyl-3,10-dioxa-7-azabicyclo[7.1.0]dec-4-ene. The resulting 9-membered azacycle generated (7-phenyl-4-tosyl-8,10-dioxa-4-azabicyclo[5. 2.1]decan-2-yl)trifluoromethanesulfonate when treated with triflic acid. Substrates with anitro or ester group at the meta-position of the phenyl produced (Z)-4-benzylidene-6-tosyl-3,9-dioxa-6-azabicyclo[6.1.0]nonane. Part 2: Iron(III)-promoted cyclization of N-((2-(hydroxymethyl)cyclopropyl)methyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide gave (Z)-3-(chloro(phenyl)methylene)-4-cyclopropyl-1-tosylpyrrolidine, while the secondary alcohol analogous generated the (Z)-5-(chloro(phenyl)methylene)-6-methyl-3-tosyl-3-azabicyclo[5.1.0]octane derivative in a diastereoselective manner.

Description

Keywords

環氧基, 氮雙環[7.1.0]癸-4-烯化合物, , , 環丙基, 甲苯磺醯基吡咯啶, 辛烷化合物, epoxy, azabicyclo[7.1.0]dec-4-ene, Gold, Iron, cyclopropyl, tosylpyrrolidine, octane

Citation

Collections