Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex.
3-diphenylhydroxymethyl-substituted BINOL-titanium complex prepared in situ was found to be a highly efficient catalyst for hetero-Diels-Alder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to 99% yield and 99% ee.
Yang
Xin-Bin
XB
Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), and West China Hospital, West China Medical School, Sichuan University, Chengdu, Sichuan 610041, PR China.
Feng
Jie
J
Zhang
Ji
J
Wang
Na
N
Wang
Li
L
Liu
Jun-Liang
JL
Yu
Xiao-Qi
XQ
D000447:Aldehydes / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000447:Aldehydes; C406944:BINOL, naphthol; D002070:Butadienes; D009284:Naphthols; D014025:Titanium