A highly efficient and stereospecific borane reduction of spiro[4.4]nonane-1,6-dione catalyzed by a chiral oxazaborolidine

Tetrahedron Letters

Volumn 41, Issue 22, 2000, Pages 4425-4429

  Lin, Ching Wen ^a   Lin, Chi Ching ^a   Li, Yue Ming ^a   Chan, Albert S C ^a  

^a HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Asymmetric reactions; Oxazaborolidine; Reduction; Spiro compounds

Indexed keywords

AZELAIC ACID; BORANE DERIVATIVE; DIKETONE; OXAZABOROLIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; CIS TRANS ISOMERISM; ENANTIOMER; RACEMIC MIXTURE; REDUCTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034622089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00606-7     Document Type: Article

References (28)

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27. f values are given as follows: 0.57 (1), 0.33 (2), 0.2 (3). For information on characterization of compound 1, please refer to: J. Am. Chem. Soc. 1959, 81, 2729. As for compounds 2 and 3, see Ref. 2b.
28. 3N (0.5 mL) in refluxing THF (2.5 mL) for 2 h to obtain the corresponding triflate derivative. After the usual extraction workup, the triflate product was then analyzed by GC with a Chrompack Chirasil-DEX CB capillary column (25 m) for the determination of enantiomeric excesses. The ee values of compound 3 can be determined directly under similar GC conditions without any further transformations. The analytical conditions and the retention times are listed in the following: Oven temperature: 110°C, carrier pressure (nitrogen): 15 psi. (1S,5S,6R)-triflate isomer of 2: 10.5 min; (1S,5R,6R)-triflate isomer of 2: 10.9 min. Oven temperature: 180°C; carrier pressure (nitrogen): 15 psi. (1R,2S,6R)-isomer of 3: 6.7 min; (1S,5R,6S)-isomer of 3: 7 min.