Enantioselective cyclopropanation reactions with planar-chiral pyridinium ylides: A substituent effect and a remote steric effect

Advanced Synthesis and Catalysis

Volumn 352, Issue 17, 2010, Pages 2966-2978

  Kanomata, Nobuhiro ^a,b   Sakaguchi, Ryo ^a   Sekine, Kazuki ^b   Yamashita, Satomi ^b   Tanaka, Hiroko ^a  

^a WASEDA UNIVERSITY   (Japan)

^b MEIJI UNIVERSITY   (Japan)

Author keywords

cyclophanes; cyclopropanes; enantioselectivity; heterocycles; planar chirality; ylides

Indexed keywords

EID: 78649573380     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000079     Document Type: Article

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53. See Experimental Section.
54. 2 are 0.0458 and 0.1271, respectively [I> 2.00s(I)]. Flack parameter (Friedel pairs=1402): -1.2(15). Crystallographic data (excluding structure factors) for the structure of (1R,3S)- 17eq have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 759773. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam. ac.uk].
55. A crystalline sample used for the X-ray analysis was confirmed to be identical with the major stereoisomer, (-)- 17eq, by measuring a CD spectrum of the recovered isomer.
56. [14]
57. Theoretical calculations were performed on a Mac Spartan 08, Wavefunction Inc., Irvine, CA, USA. All semi-empirical calculations of AM1, RM1, and PM3 methods also supported the proposal that TS-E is energetically preferable to TS-F.