Efficiency in nonenzymatic kinetic resolution

Angewandte Chemie - International Edition

Volumn 44, Issue 26, 2005, Pages 3974-4001

  Vedejs, Edwin ^a   Jure, Mara ^a,b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b RIGA TECHNICAL UNIVERSITY   (Latvia)

Author keywords

Diastereoselectivity; Enantiomer resolution; Enantioselectivity; Kinetic resolution; Stereochemistry

Indexed keywords

ASSAYS; CARBON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTIMIZATION; PROBLEM SOLVING; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

NONENZYMATIC KINETIC RESOLUTIONS; RACEMIC SUBSTRATES; STEREO CONTROLLED SYNTHESIS; WALDEN INVERSION;

REACTION KINETICS;

EID: 21344465658     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460842     Document Type: Review

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378. KR by olefin metathesis: O. Fujimura, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 2499-2500;
379. J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1998, 120, 4041-4042;
380. D. S. La, J. B. Alexander, D. R. Cefalo, D. D. Graf, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 1998, 120, 9720-9721;
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382. S. J. Dolman, E. S. Satteley, A. H. Hoveyda, R. R. Schrock, J. Am. Chem. Soc. 2002, 124, 6991-6997.
383. KR by alkene hydrogenation: Hydroxyalkylacrylates: a) J. M. Brown, I. Cutting, J. Chem. Soc. Chem. Commun. 1985, 578-579;
384. Allylic alcohols: b) M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem. 1988, 53, 708-710;
385. J. W. Faller, M. Tokunaga, Tetrahedron Lett. 1993, 34, 7359-7362;
386. Aminoalkylacrylates: c) M. Takagi, K. Yamamoto, Tetrahedron 1991, 47, 8869-8882;
387. α,β-Unsaturated acids: d) W. Leitner, J. M. Brown, H. Brunner, J. Am. Chem. Soc. 1993, 115, 152-159.
388. C. R. Baar, C. J. Levy, E. Y.-J. Min, L. M. Henling, M. W. Day, J. E. Bercaw, J. Am. Chem. Soc. 2004, 126, 8216-8231.
389. Ynal cyclization: a) M. Imai, M. Tanaka, H. Suemune, Tetrahedron 2001, 57, 1205-1211;
390. b) K. Tanaka, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 10296-10297;
391. Enyne cyclization: c) A. Lei, M. He, X. Zhang, J. Am. Chem. Soc. 2003, 125, 11472-11473.
392. Racemic dienophiles: a) B. Wegener, M. Hansen, E. Winterfeldt, Tetrahedron: Asymmetry 1993, 4, 345-350;
393. M. Goeres, E. Winterfeldt, J. Chem. Soc. Perkin Trans, 1 1994, 3525-3531;
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395. M. C. Carreno, S. Garcie-Cerrada, A. Urbano, C. D. Vitta, Tetrahedron: Asymmetry 1998, 9, 2965-2969.
396. Chiral amines and 1-acetyl-trans-cyclooctene: a) F. Henin, J. Muzart, J. P. Pete, H. Rau, Tetrahedron Lett. 1990, 31, 1015-1016;
397. F. Henin, J. Muzart, J. P. Pete, H. Rau, New J. Chem. 1992, 16, 979-985:
398. ortho-photocycloaddition of double bonds to benzene rings:b) P. J. Wagner, K. McMahon, J. Am. Chem. Soc. 1994, 116, 10827-10828;
399. 1,3-dipolar cycloadditions: c) F. Cardona, A. Gotti, A. Brandi, Eur. J. Org. Chem. 2001, 2999-3011.
400. a) J. F. Larrow, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 12129-12130;
401. b) J. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420-7421;
402. c) B. D. Brandes, E. N. Jacobsen, Tetrahedron: Asymmetry 1997, 8, 3927-3933;
403. d) M. E. Furrow, S. E. Schaus, E. N. Jacobsen, J. Org. Chem. 1998, 63, 6776-6777;
404. e) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 6086-6087;
405. f) M. H. Wu, K. B. Hansen, E. N. Jacobsen, Angew. Chem. 1999, 111, 2167-2170;
406. Angew. Chem. Int. Ed. 1999, 38, 2012-2014;
407. Polymer-supported salen catalysts: g) S. Peukert, E. N. Jacobsen, Org. Lett. 1999, 1, 1245-1248;
408. Dendrimeric salen catalysts: h) R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753;
409. Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
410. Oligomeric catalysts: i) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688;
411. j) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315;
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413. l) S. K. Kim, E. N. Jacobsen, Angew. Chem. 2004, 116, 4042-4044;
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416. a) P. S. Savle, M. J. Lamoreaux, J. F. Berry, R. D. Gandour, Tetrahedron: Asymmetry 1998, 9, 1843-1846;
417. b) C. Jin, R. D. Ramirez, A. S. Gopalan, Tetrahedron Lett. 2001, 42, 4747-4750;
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421. f) S. Chow, W. Kitching, Tetrahedron: Asymmetry 2002, 13, 779-793;
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426. KR of epoxides: a) Organoaluminum reagents: Y. Naruse, T. Esaki, H. Yamamoto, Tetrahedron Lett. 1988, 29, 1417-1420;
427. Chiral titanium complex: b) A. Ishikawa, T. Katsuki, Tetrahedron Lett. 1991, 32, 3547-3550;
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432. f) M. Asami, S. Sato, K. Honda, S. Inoue, Heterocycles 2000, 52, 1029-1032;
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440. a) R. F. Ismagilov, J. Org. Chem. 1998, 63, 3772-3774;
441. b) T. O. Lukas, C. Girard, D. R. Fenwick, H. B. Kagan, J. Am. Chem. Soc. 1999, 121, 9299-9306;
442. c) D. W. Johnson, Jr., D. A. Singleton, J. Am. Chem. Soc. 1999, 121, 9307-9312;
443. d) D. G. Blackmond, J. Am. Chem. Soc. 2001, 123, 545-553.
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445. D. E. Ward, D. How, Y. Liu, J. Am. Chem. Soc. 1997, 119, 1884-1894.
446. a) Chemical calculations program "Magnus": http://www.ch.cam. ac.uk./magnus (J. M. Goodman et al.);
447. b) J. M. Goodman, A.-K. Köhler, S. C. M. Alderton, Tetrahedron Lett. 1999, 40, 8715-8718.
448. Program "Selectivity": http://www.cis.TUGraz.at/orgc (K. Faber, H. Honig: Windows version;
449. Program "Selectivity": K. Faber, A. Kleewein: Mac version).
450. a) M. G. Finn, Chirality 2002, 14, 534-540;
451. b) A. Horeau, A. Nouaille, Tetrahedron Lett. 1990, 31, 2707-2710;
452. J. Guo, J. Wu, G. Siuzdak, M. G. Finn, Angew. Chem. 1999, 111, 1868-1871;
453. Angew. Chem. Int. Ed. 1999, 38, 1755-1758;
454. M. T. Reetz, M. H. Becker, H.-W. Klein, D. Stockigt, Angew. Chem. 1999, 111, 1872-1875:
455. Angew. Chem. Int. Ed. 1999, 38, 1758-1761;
456. D. D. Diaz, S. Yao, M. G. Finn, Tetrahedron Lett. 2001, 42, 2617-2619.
457. G. T. Copeland, S. J. Miller, J. Am. Chem. Soc. 2001, 123, 6496-6502.
458. M. T. Reetz, K. M. Kuhling, S. Wilensek, H. Husmann, U. W. Hausig, M. Hermes, Catal. Today 2001, 67, 389-396;
459. G. A. Korbel, L. Gojko, M. D. Shair, J. Am. Chem. Soc., 2001, 123, 361-362.
460. B. Dominguez, N. S. Hodnett, G. C. Lloyd-Jones, Angew. Chem. 1999, 111, 4419-4421;
461. Angew. Chem. Int. Ed. 2001, 40, 4289-4291.
462. H.-J. Gais, T. Jagusch, O. Bondarev, J. Org. Chem. 2004, 69, 2731-2736.
463. L. M. Mediavilla, A. Alexakis, N. Krause, Tetrahedron Lett. 2002, 43, 7887-7890.