TY - JOUR
T1 - Catalytic Asymmetric Synthesis of α-Trifluoromethylated Carbinols
T2 - A Case Study of Tertiary Propargylic Alcohols
AU - Noda, Hidetoshi
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
Our research identified six comparisons of LPG and diesel fuel-economy made by Governments, manufacturers and testing labs (European LPG Association, 1999; Alternative Fuels Group, 2000; Wang and Huang, 1999; Volvo Car Corporation, 2002; Australian Greenhouse Office, 2001; plus one from the International Energy Agency’s CADDET programme that has since been removed from the world-wide web where it was posted). Three said the distance travelled per volume of diesel is 1.7 times greater than per equal volume of LPG. Two said 1.6, and one said 1.8. We used the mode of 1.7.
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/4
Y1 - 2018/4
N2 - Enantioenriched CF3-substituted tertiary alcohols have been applied in a broad range of chemical disciplines, including medicinal chemistry and agrochemistry. The widely prescribed anti-HIV pharmaceutical efavirenz is one particular example of the application of these chiral building blocks. Because the typical synthetic route to this small drug molecule involves the stoichiometric use of a chiral promoter, significant effort has been devoted to the development of catalytic alternatives for accessing this building block. In this Focus Review, we summarize the catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols based on three retrosynthetic approaches, namely one trifluoromethylation approach and two building-block strategies. The general challenges that are involved in the construction of a CF3-substituted tetrasubstituted stereogenic carbon species are highlighted and possible future directions in the field are discussed.
AB - Enantioenriched CF3-substituted tertiary alcohols have been applied in a broad range of chemical disciplines, including medicinal chemistry and agrochemistry. The widely prescribed anti-HIV pharmaceutical efavirenz is one particular example of the application of these chiral building blocks. Because the typical synthetic route to this small drug molecule involves the stoichiometric use of a chiral promoter, significant effort has been devoted to the development of catalytic alternatives for accessing this building block. In this Focus Review, we summarize the catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols based on three retrosynthetic approaches, namely one trifluoromethylation approach and two building-block strategies. The general challenges that are involved in the construction of a CF3-substituted tetrasubstituted stereogenic carbon species are highlighted and possible future directions in the field are discussed.
KW - alcohols
KW - alkynes
KW - asymmetric catalysis
KW - fluorine
KW - synthetic methods
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U2 - 10.1002/ajoc.201800013
DO - 10.1002/ajoc.201800013
M3 - Review article
AN - SCOPUS:85042173393
SN - 2193-5807
VL - 7
SP - 599
EP - 612
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 4
ER -
