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A Regioselective Cyclohexannulation Procedure via Dienamine [4 + 2] Cycloaddition. Synthesis of Functionalised Decalins
Author(s) -
Snowden Roger L.,
Linder Simon M.,
Wüst Manfred
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720505
Subject(s) - chemistry , regioselectivity , cycloaddition , bicyclic molecule , context (archaeology) , methyl acrylate , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , polymer , paleontology , copolymer , biology
A regioselective cyclohexannulation procedure, whose key step involves the [4 + 2] cycloaddition of dienamines 12–24 with methyl acrylate, allows the conversion of cycloalkanones 1–11 to bicyclic dienoates 25 – 37 . The chemistry of 26 is briefly examined and, in the context of organoleptic studies concerning functionalised 5,5,9‐tri‐methyldecalins, the transformation of 37 to ketones 44 and 46 as well as to acetates 53–56 is described.