Discovery of exceptionally efficient catalysts for solvent-free enantioselective hetero-Diels-Alder reaction.
Combinatorial coordination chemistry strategy combined with high-throughput screening techniques has been successfully applied to engineering practical enantioselective catalysts for asymmetric hetero-Diels-Alder reaction. The reaction of Danishefsky's diene with a variety of aldehydes can be carried out with 0.1-0.005 mol % of H4-BINOL/Ti/H4-BINOL or H4-BINOL/Ti/H8-BINOL catalysts at room temperature under solvent- and MS-free conditions to afford dihydropyrone derivatives with up to quantitative yield and 99.8% ee.
Long
Jiang
J
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China.
Hu
Jieyu
J
Shen
Xiaoqiang
X
Ji
Baoming
B
Ding
Kuiling
K
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D009284:Naphthols / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis*; D012997:Solvents; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000447:Aldehydes; D000475:Alkenes; C406944:BINOL, naphthol; D009284:Naphthols; D009942:Organometallic Compounds; D011753:Pyrones; D012997:Solvents; D014025:Titanium