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Experimental and Theoretical Investigation of Hydrogenative Cyclization of Allenynes
Author(s) -
Kim HyoTong,
Yoon HyoSang,
Jang WooYoung,
Kang Youn K.,
Jang HyeYoung
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100280
Subject(s) - chemistry , stereoselectivity , catalysis , stoichiometry , platinum , catalytic cycle , deuterium , hydrogen , organic chemistry , combinatorial chemistry , group 2 organometallic chemistry , computational chemistry , molecule , physics , quantum mechanics
Upon platinum‐catalyzed hydrogenation, allenynes underwent reductive cyclization to provide hetero‐ and carbocycles with completely controlled regio‐ and stereoselectivity. By employing hydrogen as a reductant, the use of stoichiometric amounts of toxic organometallic reductants was avoided, leading to clean and cost‐effective synthesis. A possible catalytic cycle is proposed on the basis of a deuterium‐labeling study and theoretical calculations.