Stereocontrolled construction of tetrahydrofurans and gamma-butyrolactones using organomolybdenum chemistry.
[reaction: see text]. Diastereoselective conversion of pi-allylmolybdenum complex aldehyde 1 to organometallic triol 4 and diols 5, 10, and 13 is described. Stereocontrolled demetalation of 4, 5, and 13 was accomplished, leading to hydroxylated tetrahydrofurans and gamma-butyrolactones, as single diastereoisomers.
Pearson
A J
AJ
Department of Chemistry, Case Western Reserve University, Cleveland, Ohio 44106, USA. ajp4@po.cwru.edu
Mesaros
E F
EF
D015107:4-Butyrolactone / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D008982:Molybdenum / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D009942:Organometallic Compounds; C018674:tetrahydrofuran; D008982:Molybdenum; D015107:4-Butyrolactone