Zirconium-Catalyzed Kinetic Resolution of Cyclic Allylic Ethers. An Enantioselective Route to Unsaturated Medium Ring Systems

1996 ◽  
Vol 118 (15) ◽  
pp. 3779-3780 ◽  
Author(s):  
Michael S. Visser ◽  
Joseph P. A. Harrity ◽  
Amir H. Hoveyda
Keyword(s):  
Kinetic Resolution ◽  
Ring Systems ◽  
Medium Ring ◽  
Allylic Ethers

ChemInform Abstract: Cyclizations of Hydroxy Dithioketals. New Synthetic Technology for the Construction of Oxocenes and Related Medium-Ring Systems.

ChemInform ◽  
1989 ◽  
Vol 20 (43) ◽  
Author(s):  
K. C. NICOLAOU ◽  
C. V. C. PRASAD ◽  
C.-K. HWANG ◽  
M. E. DUGGAN ◽  
C. A. VEALE
Keyword(s):  
Ring Systems ◽  
Medium Ring

Synthesis of some 2,5-benzoxazocine and 2,6-benzoxazonine derivatives from ω-(Dihydroisoindol-2-yl)alkanol precursors by means of cyanogen bromide

1982 ◽  
Vol 35 (11) ◽  
pp. 2307 ◽  
Author(s):  
JB Bremner ◽  
N Thirasasana
Keyword(s):  
Cyanogen Bromide ◽  
Ring Systems ◽  
Derivatives Of ◽  
Medium Ring ◽  
Moderate Yield

Reaction of cyanogen bromide with 2-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)ethanol (5a) gave 1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine-5-carbonitrile (6a) in a low to moderate yield. Similarly, 3-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)propan-1-ol (5c) gave 1-phenyl-1,3,4,5,6,7-hexa-hydro-2,6-benzoxazonine-6-carbonitrile (6c). The analogous 1-(4-methoxyphenyl) derivatives of both medium ring systems were also prepared, and some mechanistic aspects of the results are discussed. Conversion of (6a) into the analgesic, Nefopam,is described.

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