BINOL-Al catalysed asymmetric cyclization and amplification: preparation of optically active menthol analogs.
We report a highly selective asymmetric ring-closing ene reaction catalysed by aluminum complexes with chiral BINOL. This reaction yields optically active 6-membered cyclized alcohols from unsaturated aldehydes, with good diastereo- and enantioselectivities. Asymmetric amplification of this reaction was investigated by varying the ee of the BINOL employed in the catalyst.
Takasago International Corporation, 4-11, Nishi-Yawata 1-Chome, Hiratsuka City, Kanagawa 254-0073, Japan. yoji_hori@takasago.com.
Hisanori
H
Itoh
Hironori
H
Maeda
Shinya
S
Yamada
Yoji
Y
Hori
Takashi
T
Mino
Masami
M
Sakamoto
D000447:Aldehydes / Q000737:chemistry*; D017607:Aluminum Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008610:Menthol / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D017607:Aluminum Compounds; C406944:BINOL, naphthol; D009284:Naphthols; D008610:Menthol