Gold-catalyzed tandem C-C and C-O bond formation: a highly diastereoselective formation of cyclohex-4-ene-1,2-diol derivatives.
We have reported an efficient gold(I)-catalyzed tandem cyclization of tert-butyl carbonate derivatives of hex-1-en-5-yn-3-ol where nucleophilic participation of the O-Boc group appears to intercept a carbocationic (or cyclopropyl carbene) Au intermediate. This novel protocol leads to densely functionalized cyclohexene-3,4-diol derivatives where 1,2- or 1,2,3-stereocenters are controlled in a highly diastereoselective fashion.
Department of Chemistry, Hanyang University, Seoul Korea 133-791.
Choongmin
C
Lim
Ji-Eun
JE
Kang
Ji-Eun
JE
Lee
Seunghoon
S
Shin
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013237:Stereoisomerism
D053138:Cyclohexenes; D002244:Carbon; D006046:Gold; D010100:Oxygen