Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary

碩士 === 國立清華大學 === 化學系 === 103 === This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester...

Full description

Bibliographic Details
Main Authors:	Liao, De Jhong, 廖得仲
Other Authors:	Uang, Biing Jiun
Format:	Others
Language:	zh-TW
Published:	2015
Online Access:	http://ndltd.ncl.edu.tw/handle/g56v6u

id	ndltd-TW-103NTHU5065124
record_format	oai_dc
spelling	ndltd-TW-103NTHU50651242019-05-15T22:18:04Z http://ndltd.ncl.edu.tw/handle/g56v6u Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary 樟腦醯胺為掌性輔助基應用於 (+)-2-epi-α-Allokainic Acid 之不對稱合成研究 Liao, De Jhong 廖得仲碩士國立清華大學化學系 103 This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester 142 afforded adduct 130 as a single isomer. Transamination of compound 130, followed by cyclization provided lactam 147. The construction of C4 stereogenic center was achieved by the aldol reaction of boc-protected lactam 147 with acetone. Further functional group transformation led to the synthesis of (+)-2- epi-α-Allokainic acid 128. Uang, Biing Jiun 汪炳鈞 2015 學位論文 ; thesis 87 zh-TW
collection	NDLTD
language	zh-TW
format	Others
sources	NDLTD
description	碩士 === 國立清華大學 === 化學系 === 103 === This thesis deals with the application of camphor-derived ketopinic amide 139 as a chiral auxiliary in the synthesis of pyrrolidine alkaloids. Asymmetric 1,4-addition of chiral imine 116, derived from glycinate 142 and ketopinic amide 139, with α,β-unsaturated ester 142 afforded adduct 130 as a single isomer. Transamination of compound 130, followed by cyclization provided lactam 147. The construction of C4 stereogenic center was achieved by the aldol reaction of boc-protected lactam 147 with acetone. Further functional group transformation led to the synthesis of (+)-2- epi-α-Allokainic acid 128.
author2	Uang, Biing Jiun
author_facet	Uang, Biing Jiun Liao, De Jhong 廖得仲
author	Liao, De Jhong 廖得仲
spellingShingle	Liao, De Jhong 廖得仲 Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
author_sort	Liao, De Jhong
title	Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
title_short	Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
title_full	Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
title_fullStr	Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
title_full_unstemmed	Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary
title_sort	asymmetric synthesis of (+)-2-epi-α-allokainic acid employing ketopinic amide as chiral auxiliary
publishDate	2015
url	http://ndltd.ncl.edu.tw/handle/g56v6u
work_keys_str_mv	AT liaodejhong asymmetricsynthesisof2epiaallokainicacidemployingketopinicamideaschiralauxiliary AT liàodézhòng asymmetricsynthesisof2epiaallokainicacidemployingketopinicamideaschiralauxiliary AT liaodejhong zhāngnǎoxīànwèizhǎngxìngfǔzhùjīyīngyòngyú2epiaallokainicacidzhībùduìchēnghéchéngyánjiū AT liàodézhòng zhāngnǎoxīànwèizhǎngxìngfǔzhùjīyīngyòngyú2epiaallokainicacidzhībùduìchēnghéchéngyánjiū
_version_	1719128612258447360

Asymmetric Synthesis of (+)-2-epi-α-Allokainic Acid Employing Ketopinic Amide as Chiral Auxiliary

Similar Items