Phosphane‐Catalyzed Annulation of Allenoates with 3‐Nitro‐2H‐chromenes: Synthesis of Tetrahydrocyclopentachromenes

The synthesis of carbocyclic‐fused chromene derivatives based on allene chemistry is described. The phosphane‐catalyzed [3+2] annulation reactions of allenic esters with 3‐nitrochromenes have been established affording 3a‐nitro‐tetrahydrocyclopenta[c]chromenes in good yields (up to 87 %) with high s...

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Veröffentlicht in:	European journal of organic chemistry 2019-09, Vol.2019 (31-32), p.5441-5451
Hauptverfasser:	Soares, Maria I L, Gomes, Clara S B, Nunes, Sandra C C, Alberto A C C Pais, Teresa M V D Pinho e Melo
Format:	Artikel
Sprache:	eng
Schlagworte:	Allene Amines Chemical reactions Esters Organic chemistry Quantum chemistry Regioselectivity Selectivity
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creator	Soares, Maria I L Gomes, Clara S B Nunes, Sandra C C Alberto A C C Pais Teresa M V D Pinho e Melo
description	The synthesis of carbocyclic‐fused chromene derivatives based on allene chemistry is described. The phosphane‐catalyzed [3+2] annulation reactions of allenic esters with 3‐nitrochromenes have been established affording 3a‐nitro‐tetrahydrocyclopenta[c]chromenes in good yields (up to 87 %) with high stereo‐ and regioselectivity. Quantum chemical calculations, carried out at the DFT level of theory, were in agreement with the observed selectivity. The trichlorosilane‐mediated reduction of the 3a‐nitro‐tetrahydrocyclopenta[c]chromenes into the corresponding amines is also reported.
doi_str_mv	10.1002/ejoc.201900564
format	Article
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The phosphane‐catalyzed [3+2] annulation reactions of allenic esters with 3‐nitrochromenes have been established affording 3a‐nitro‐tetrahydrocyclopenta[c]chromenes in good yields (up to 87 %) with high stereo‐ and regioselectivity. Quantum chemical calculations, carried out at the DFT level of theory, were in agreement with the observed selectivity. The trichlorosilane‐mediated reduction of the 3a‐nitro‐tetrahydrocyclopenta[c]chromenes into the corresponding amines is also reported.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201900564</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Allene ; Amines ; Chemical reactions ; Esters ; Organic chemistry ; Quantum chemistry ; Regioselectivity ; Selectivity</subject><ispartof>European journal of organic chemistry, 2019-09, Vol.2019 (31-32), p.5441-5451</ispartof><rights>2019 WILEY‐VCH Verlag GmbH & Co. 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The phosphane‐catalyzed [3+2] annulation reactions of allenic esters with 3‐nitrochromenes have been established affording 3a‐nitro‐tetrahydrocyclopenta[c]chromenes in good yields (up to 87 %) with high stereo‐ and regioselectivity. Quantum chemical calculations, carried out at the DFT level of theory, were in agreement with the observed selectivity. The trichlorosilane‐mediated reduction of the 3a‐nitro‐tetrahydrocyclopenta[c]chromenes into the corresponding amines is also reported.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201900564</doi></addata></record>
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subjects	Allene Amines Chemical reactions Esters Organic chemistry Quantum chemistry Regioselectivity Selectivity
title	Phosphane‐Catalyzed Annulation of Allenoates with 3‐Nitro‐2H‐chromenes: Synthesis of Tetrahydrocyclopentachromenes
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