Brucine Diol–Copper-Catalyzed Asymmetric Synthesis of endo-Pyrrolidines: The Mechanistic Dichotomy of Imino Esters

Enantio- and diastereodivergent approaches to pyrrolidines are described by using catalyst- and substrate-controlled reaction pathways. A concerted endo-selective [3 + 2]-cycloaddition pathway is developed for the reaction of methyl imino ester, whereas endo-pyrrolidines with an opposite absolute st...

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Veröffentlicht in:	Organic letters 2015-03, Vol.17 (5), p.1288-1291
Hauptverfasser:	Li, Jian-Yuan, Kim, Hun Young, Oh, Kyungsoo
Format:	Artikel
Sprache:	eng
Schlagworte:	Azo Compounds - chemical synthesis Azo Compounds - chemistry Catalysis Copper - chemistry Molecular Structure Pyrrolidines - chemical synthesis Pyrrolidines - chemistry Stereoisomerism Strychnine - analogs & derivatives Strychnine - chemistry Thiosemicarbazones - chemical synthesis Thiosemicarbazones - chemistry
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creator	Li, Jian-Yuan Kim, Hun Young Oh, Kyungsoo
description	Enantio- and diastereodivergent approaches to pyrrolidines are described by using catalyst- and substrate-controlled reaction pathways. A concerted endo-selective [3 + 2]-cycloaddition pathway is developed for the reaction of methyl imino ester, whereas endo-pyrrolidines with an opposite absolute stereochemical outcome are prepared by using the stepwise reaction pathway of tert-butyl imino ester. The development of catalyst- and substrate-controlled stereodivergent approaches highlights the inherent substrate–catalyst interactions in the [3 + 2]-cycloaddition reactions of metalated azomethine ylides.
doi_str_mv	10.1021/acs.orglett.5b00277
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Lett</addtitle><date>2015-03-06</date><risdate>2015</risdate><volume>17</volume><issue>5</issue><spage>1288</spage><epage>1291</epage><pages>1288-1291</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Enantio- and diastereodivergent approaches to pyrrolidines are described by using catalyst- and substrate-controlled reaction pathways. A concerted endo-selective [3 + 2]-cycloaddition pathway is developed for the reaction of methyl imino ester, whereas endo-pyrrolidines with an opposite absolute stereochemical outcome are prepared by using the stepwise reaction pathway of tert-butyl imino ester. The development of catalyst- and substrate-controlled stereodivergent approaches highlights the inherent substrate–catalyst interactions in the [3 + 2]-cycloaddition reactions of metalated azomethine ylides.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25695534</pmid><doi>10.1021/acs.orglett.5b00277</doi><tpages>4</tpages></addata></record>
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subjects	Azo Compounds - chemical synthesis Azo Compounds - chemistry Catalysis Copper - chemistry Molecular Structure Pyrrolidines - chemical synthesis Pyrrolidines - chemistry Stereoisomerism Strychnine - analogs & derivatives Strychnine - chemistry Thiosemicarbazones - chemical synthesis Thiosemicarbazones - chemistry
title	Brucine Diol–Copper-Catalyzed Asymmetric Synthesis of endo-Pyrrolidines: The Mechanistic Dichotomy of Imino Esters
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