Inversion of the direction of stereoinduction in the coupling of chiral gamma,delta-unsaturated Fischer carbene complexes with o-ethynylbenzaldehyde.
[reaction: see text] A variety of gamma,delta-unsaturated carbene complexes that feature a stereogenic center at the beta-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.
Ghorai
Binay K
BK
Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, New Mexico 88003, USA.
Menon
Suneetha
S
Johnson
Dennis Lee
DL
Herndon
James W
JW
D000480:Alkynes / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry*; D006838:Hydrocarbons; D007700:Kinetics; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D013816:Thermodynamics
D000480:Alkynes; D001547:Benzaldehydes; D006838:Hydrocarbons; D013256:Steroids; C413250:ethynylbenzaldehyde; C030011:carbene; D008697:Methane