Catalytic asymmetric cycloaddition of ketenes and nitroso compounds:enantioselective synthesis of α-hydroxycarboxylic acid derivatives

Angewandte Chemie - International Edition

Volumn 48, Issue 13, 2009, Pages 2391-2393

  Dochnahl, Maximilian ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Asymmetric catalysis; Carboxylic acids; Cycloaddition; Heterocycles; Ketenes

Indexed keywords

CARBOXYLIC ACIDS; CYCLOADDITION; ENANTIOSELECTIVITY; MOLECULES; NITROGEN COMPOUNDS; STEREOCHEMISTRY;

ACID DERIVATIVE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLES; KETENES; NITROSO COMPOUNDS; REGIOSELECTIVITY AND ENANTIOSELECTIVITY; TARGET MOLECULE;

REGIOSELECTIVITY;

CARBOXYLIC ACID; ETHYLENE DERIVATIVE; HETEROCYCLIC COMPOUND; KETENE; KETONE; NITROSO DERIVATIVE;

CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; ETHYLENES; HETEROCYCLIC COMPOUNDS; KETONES; NITROSO COMPOUNDS; STEREOISOMERISM;

EID: 70349786461     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805805     Document Type: Article

References (31)

1. For some leading references, see: a) G. M. Coppola, H. F. Schuster,a-Hydroxy Acids in Enantioselective Synthesis, VCH, Weinheim,1997;
2. b) H. Gröger, Adv. Synth. Catal. 2001, 343,547-558;
3. c) "Development of an Efficient Synthesis of Chiral 2-HydroxyAcids": J. Tao, K. McGee in Asymmetric Catalysis on Industrial Scale(Eds.: H. U. Blaser, E. Schmidt), Wiley-VCH, Weinheim, 2003, chap. IV.1.
4. For an overview, see: O. Riant, J. Hannedouche, Org. Biomol. Chem.2007, 5, 873-888.
5. For a pioneering example, see: Y. Hamashima, M. Kanai, M. Shibasaki,J. Am. Chem. Soc. 2000, 122, 7412-7413.
6. For two seminal studies, see: a) E. F. DiMauro, M. C. Kozlowski, J.Am. Chem. Soc. 2002, 124, 12668-12669;
7. b) K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem.2003, 115, 5647-5650;
8. Angew. Chem. Int. Ed. 2003, 42, 5489-5492.
9. T. Ooi, K. Fukumoto, K. Maruoka, Angew. Chem. 2006,118, 3923-3926;
10. Angew. Chem. Int. Ed. 2006, 45, 3839-3842.
11. For example, previously described catalytic asymmetric processes do notgenerally provide access to enantioenriched α-hydroxycarboxylic acidswherein the tertiary alcohol bears a secondary alkyl substituent or a hinderedaromatic group (see Table 2).
12. a) H. Staudinger, S. Jelagin, Ber. Dtsch. Chem. Ges. 1911,44, 365-374;
13. b) S. P. Makarov, V. A. Shpanskii, V. A. Ginsburg, A. I.; Shchekotikhin,A. S. Filatov, L. L. Martynova, I. V. Pavlovskaya, A. F. Golovaneva, A. Y.Yakubovich, Dokl. Akad. Nauk SSSR 1962, 142, 596-599;
14. c) G. Kresze, A. Trede, Tetrahedron 1963, 19,133-136;
15. d) R. C. Kerber, M. C. Cann, J. Org. Chem. 1974, 39,2552-2558;
16. e) D. Moderhack, K. Stolz, Chem. Zeit. 1990, 114,5-1.
17. To our knowledge, there are no reports of the synthesis of anenantioenriched 1,2-oxazetidin-3-one. This heterocycle has a structuralsimilarity to a β-lactam and to cycloserine.
18. a) Imines: E. C. Lee, B. L. Hodous, E. Bergin, C. Shih, G. C. Fu, J.Am. Chem. Soc. 2005, 127, 11586-11587;
19. B. L. Hodous, G. C. Fu J. Am. Chem. Soc. 2002, 124,1578-1579;
20. b) Aldehydes: J. E. Wilson, G. C. Fu, Angew. Chem. 2004,116, 6518-6520;
21. Angew. Chem. Int. Ed. 2004, 43, 6358-6360;
22. c) Azo compounds: J. M. Berlin, G. C. Fu, Angew. Chem.2008, 120, 7156-7158;
23. Angew. Chem. Int. Ed. 2008, 47, 7048-7050.
24. For excellent overviews of ketene chemistry, including investigations byothers of catalytic asymmetric [2+2] cycloadditions, see: a) T. T. Tidwell,Eur. J. Org. Chem. 2006, 563-576;
25. b) R. K. Orr, M. A. Calter, Tetrahedron 2003, 59,3545-3565.
26. The 1,2-oxazetidin-3-one is the major product of the uncatalyzed process.
27. For a discussion, see Reference [7d].
28. For uncatalyzed [2+2] cycloadditions of ketenes with nitro-soarenes, theelectronic nature of the nitrosoarene can have a moderate impact upon productdistribution (Reference [7d]).
29. When conducted on a 5 mmol scale (2% catalyst loading), the cycloadditiondepicted in Table 2, entry 10 proceeded in 96% yield (1.6 g product) and with98% ee.
30. 4 and Zn/AcOH havepreviously been described (Reference [7c]). Additional derivatizations aredescribed in the Supporting Information.
31. We do not detect a nonlinear effect: product ee value correlates linearlywith catalyst ee value.