TY - JOUR
T1 - Recent advances in the stereoselective synthesis of acyclic all-carbon tetrasubstituted alkenes
AU - Buttard, Floris
AU - Sharma, Jyoti
AU - Champagne, Pier Alexandre
N1 - Funding Information:
The preparation of this review article was supported by generous startup funds from the New Jersey Institute of Technology to P. A. C.
Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2021/4/30
Y1 - 2021/4/30
N2 - Alkenes bearing four carbon-based groups are ubiquitous motifs in chemical sciences due to their various applications from medicinal to materials chemistry, and as chemical platforms for the synthesis of complex, chiral molecules. As such, tremendous research efforts are currently ongoing in order to develop general procedures for the challenging stereoselective synthesis of all-carbon tetrasubstituted alkenes, especially for acyclic structures. Since classical approaches to carbon-carbon double bonds are not suitable for the high steric demand around tetrasubstituted alkenes, a variety of unique approaches to access these privileged functional groups have been developed in recent years. This review article highlights the most significant developments in the field from 2007 to 2020, with an emphasis on the mechanisms and remaining limitations of these contemporary methods. Specifically, recent advances in internal alkyne carbofunctionalizations, in multicomponent couplings or other cross-couplings from nucleophilic or electrophilic alkenyl partners, and in the development of miscellaneous methods, are discussed. This journal is
AB - Alkenes bearing four carbon-based groups are ubiquitous motifs in chemical sciences due to their various applications from medicinal to materials chemistry, and as chemical platforms for the synthesis of complex, chiral molecules. As such, tremendous research efforts are currently ongoing in order to develop general procedures for the challenging stereoselective synthesis of all-carbon tetrasubstituted alkenes, especially for acyclic structures. Since classical approaches to carbon-carbon double bonds are not suitable for the high steric demand around tetrasubstituted alkenes, a variety of unique approaches to access these privileged functional groups have been developed in recent years. This review article highlights the most significant developments in the field from 2007 to 2020, with an emphasis on the mechanisms and remaining limitations of these contemporary methods. Specifically, recent advances in internal alkyne carbofunctionalizations, in multicomponent couplings or other cross-couplings from nucleophilic or electrophilic alkenyl partners, and in the development of miscellaneous methods, are discussed. This journal is
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U2 - 10.1039/d1cc00596k
DO - 10.1039/d1cc00596k
M3 - Review article
C2 - 33908457
AN - SCOPUS:85104985708
SN - 1359-7345
VL - 57
SP - 4071
EP - 4088
JO - Chemical Communications
JF - Chemical Communications
IS - 34
ER -