Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines

A fast one: The title reaction proceeds in the presence of 5 mol % of the catalyst 1, and is complete within an hour. The 2‐alkyl‐ and 2‐aryl‐substituted 3‐pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of...

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Veröffentlicht in:	Angewandte Chemie International Edition 2012-01, Vol.51 (3), p.767-770
Hauptverfasser:	Han, Xiaoyu, Zhong, Fangrui, Wang, Youqing, Lu, Yixin
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkadienes - chemistry allenes Catalysis Cyclization cycloadditions Dipeptides - chemistry heterocycles Imines - chemistry nucleophilic catalysis phosphines Phosphines - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Pyrrolizidine Alkaloids - chemical synthesis
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container_title	Angewandte Chemie International Edition
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creator	Han, Xiaoyu Zhong, Fangrui Wang, Youqing Lu, Yixin
description	A fast one: The title reaction proceeds in the presence of 5 mol % of the catalyst 1, and is complete within an hour. The 2‐alkyl‐ and 2‐aryl‐substituted 3‐pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of (+)‐trachelanthamidine is also demonstrated. Boc=tert‐butoxycarbonyl, M.S.=molecular sieves, TBDPS=tert‐butyldiphenylsilyl.
doi_str_mv	10.1002/anie.201106672
format	Article
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Chem. Int. Ed</addtitle><date>2012-01-16</date><risdate>2012</risdate><volume>51</volume><issue>3</issue><spage>767</spage><epage>770</epage><pages>767-770</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A fast one: The title reaction proceeds in the presence of 5 mol % of the catalyst 1, and is complete within an hour. The 2‐alkyl‐ and 2‐aryl‐substituted 3‐pyrroline products are obtained in good yield and with high enantioselectivity. The application of the method to the concise formal synthesis of (+)‐trachelanthamidine is also demonstrated. Boc=tert‐butoxycarbonyl, M.S.=molecular sieves, TBDPS=tert‐butyldiphenylsilyl.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>22162303</pmid><doi>10.1002/anie.201106672</doi><tpages>4</tpages><edition>International ed. in English</edition></addata></record>
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subjects	Alkadienes - chemistry allenes Catalysis Cyclization cycloadditions Dipeptides - chemistry heterocycles Imines - chemistry nucleophilic catalysis phosphines Phosphines - chemistry Pyrroles - chemical synthesis Pyrroles - chemistry Pyrrolizidine Alkaloids - chemical synthesis
title	Versatile Enantioselective [3+2] Cyclization between Imines and Allenoates Catalyzed by Dipeptide-Based Phosphines
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