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Regioselective synthesis of substituted bicyclo[3.2.1]oct‐3‐ene‐2,8‐diones via double carbonylation of 1,3‐cyclohexadienes
Author(s) -
Eilbracht Peter,
Jelitte Rüdiger,
Trabold Peter
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190117
Subject(s) - chemistry , bicyclic molecule , regioselectivity , carbonylation , diketone , stereochemistry , medicinal chemistry , double bond , carbon monoxide , organic chemistry , catalysis
Abstract Double carbonylation of 1,3‐cyclohexadienes 1 is applied to the synthesis of substituted bicyclo[3.2.1]oct‐3‐ene‐2,8‐diones 4 . The Lewis acid mediated ring enlargement of substituted cyclohexadiene complexes 2 produces the cycloheptanone alkyl allyl complexes 3 with high regioselectivity. Substituted bicyclic diketones 4 are obtained in high yields by treating the complexes 3 with carbon monoxide under pressure or by oxidative decomposition. The two carbonylation steps can also be performed in a one‐pot version.