Enantioselective synthesis of planar chiral organonitrogen cycles

Journal of the American Chemical Society

Volumn 132, Issue 27, 2010, Pages 9232-9233

  Tomooka, Katsuhiko ^a   Uehara, Kazuhiro ^a,b   Nishikawa, Rie ^b   Suzuki, Masaki ^b   Igawa, Kazunobu ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE SYNTHESIS; LINEAR PRECURSORS;

CYCLIZATION;

ORGANONITROGEN DERIVATIVE;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; PRECURSOR; STOICHIOMETRY; SYNTHESIS;

EID: 77955789874     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1024657     Document Type: Article

References (31)

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4. (a) Tomooka, K.; Suzuki, M.; Uehara, K.; Shimada, M.; Akiyama, T. Synlett 2008, 2518.
5. (b) Tomooka, K.; Akiyama, T.; Man, P.; Suzuki, M. Tetrahedron Lett. 2008, 49, 6327.
6. Separation of (±)-1 is effected by (i) HPLC with a semipreparative chiral stationary phase column, by (ii) kinetic resolution with asymmetric transformations and by (iii) fractional crystallization of ammonium salt prepared from 1 (Y = H) and chiral acids. For details, see ref 1a.
7. Elegant asymmetric syntheses of planar chiral cycloalkenes have been reported. Stereospecific transformation using central chirality in the precursor:
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19. Substrate 7a was prepared from nerol in four steps; see Supporting Information.
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21. Chiral PTC 8a and 8b were prepared according to reported procedures:
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23. (b) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353. 8c was newly synthesized from cinchonidine. 9 was newly synthesized from cinchonine which is well konwn as a surrogate for the antipode of cinchonidine; see:
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25. 4 pOMe, or 9-anthracenylmethyl group and that of X from Cl to Br or I caused no remarkable improvement in terms of enantioselectivity.
26. Alkoxides 10 and 11 were prepared from cinchonidine or cinchonine with n-BuLi.
27. We have separately reported that 12 acts as an efficient CP for enantioselective Stevens rearrangement: Tomooka, K.; Sakamaki, J.; Harada, M.; Wada, R. Synlett 2008, 683.
28. More than 2 equiv of 13 or 14 only improved the chemical yields, while the enantioselectivity remained roughly constant.
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31. Performed with Gaussian 03 on a TSUBAME system at Tokyo Institute of Technology.