Asymmetric Diels-Alder reaction catalyzed by a chiral titanium reagent

✍ Scribed by Narasaka, Koichi; Iwasawa, Nobuharu; Inoue, Masayuki; Yamada, Tohru; Nakashima, Masako; Sugimori, Jun

• Book ID: 120082918
• Publisher: American Chemical Society
• Year: 1989
• Tongue: English
• Weight: 813 KB
• Volume: 111
• Category: Article
• ISSN: 0002-7863
• DOI: 10.1021/ja00196a045

✦ Synopsis

Reaction of Cis Hydroxy Epoxide 63 with Dimsylpotassium. Preparat ion of ( 1 S *, 1 'S * ,3'R * ,8'S *) -1 -(2',7'-Dioxabic y clo[ 4.4.01decan-3'yl)-2-propanol (65) and Its Acetate ( ). The bicyclic compound 65 was prepared from compound 63 (19.8 mg, 0.1 mmol) by the same procedure used to convert 61 to 64. Flash chromatography (silica, 40% ether in petroleum ether) gave compound 65 (19.0 mg, 96%). Compound 65 also can be prepared from compound 63 (19.8 mg, 0.1 mmol) by the same procedure used to convert 61 to 62 via acid catalysis. (9.0 mg, 45% after flash column chromatography). 65: oil; RJ = 0.47 (silica, 60% ether in petroleum ether); [(YI2,D +7.0° (c 0.1, CH,CI,); IR (neat)