Chiral tertiary 2-furyl alcohols: diversified key intermediates to bioactive compounds. Their enantioselective synthesis via (2-furyl)aluminium addition to ketones catalyzed by a titanium catalyst of (S)-BINOL.
Novel asymmetric 2-furyl additions of (2-furyl)AlEt(2)(THF) to aromatic ketones and one alpha,beta-unsaturated ketone catalyzed by a titanium catalyst of 10-20 mol% (S)-BINOL are reported to furnish tertiary furyl alcohols in good to excellent enantioselectivities of 87-93% ee.
Wu
Kuo-Hui
KH
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan, Republic of China.
Chuang
Da-Wei
DW
Chen
Chien-An
CA
Gau
Han-Mou
HM
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000535:Aluminum / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; C406944:BINOL, naphthol; D005663:Furans; D007659:Ketones; D009284:Naphthols; D009942:Organometallic Compounds; D000535:Aluminum; D014025:Titanium