PdII/PdIV Catalytic Enantioselective Synthesis of Bicyclo[3.1.0]hexanes via Oxidative Cyclization of Enynes

Journal of the American Chemical Society

Volumn 131, Issue 10, 2009, Pages 3452-3453

  Tsujihara, Tetsuya ^a   Takenaka, Kazuhiro ^b   Onitsuka, Kiyotaka ^b   Hatanaka, Minoru ^a   Sasai, Hiroaki ^b  

^a OSAKA UNIVERSITY   (Japan)

^b IWATE MEDICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRAL LIGAND; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; HYPERVALENT IODINE REAGENTS; OXIDATIVE CYCLIZATION;

CHELATION; CYCLIZATION; HEXANE; IODINE; PALLADIUM;

PALLADIUM COMPOUNDS;

CYCLOHEXANE DERIVATIVE; PALLADIUM; BICYCLO COMPOUND; BICYCLO(3.1.0)HEXANE;

ARTICLE; CYCLIZATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

BICYCLO COMPOUNDS; CATALYSIS; CYCLIZATION; OXIDATION-REDUCTION; PALLADIUM; STEREOISOMERISM;

EID: 68249145558     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja809965e     Document Type: Article

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27. Since NMR data of 2a are very consistent with those reported in ref 6b, the relative configuration is certainly established as depicted.
28. Abbreviations: (R)-BINAP ) (R)-2,2'-bis(diphenylphosphino)-1,1'- binaphthyl; (S,S)-t-Bu-BOX ) 2,2-bis[(4S)-4-tert-butyl-2-oxazolin-2-yl]propane; (S,S)-i-Pr-BOXAX ) (S)-2,2'-bis[(4S)-4-isopropyl-2-oxazolin-2-yl]-1,1'- binaphthyl.
29. The results using other SPRIX ligands: 3b: 88% yield, 60% ee; 3c: 91% yield, 59% ee; 3d: 65% yield, 25% ee. See Supporting Information.
30. Although improvement of the enantioselectivity was also observed for other substrates by using PhI(OCOCF3)2, the chemical yield was drastically diminished: for example, 1a: 32% yield, 96% ee.
31. Preliminary examination using enyne substrates with either an ether or an amide linkage gave an inseparable mixture in each case.
32. The absolute configuration of the products is tentatively assigned to be (1R,5S) by comparison of the sign of optical rotation with the value for a similar compound reported in refs 8a and 8c.