Phosphine-catalyzed formation of carbon-sulfur bonds: Catalytic asymmetric synthesis of γ-thioesters

Journal of the American Chemical Society

Volumn 132, Issue 13, 2010, Pages 4568-4569

  Sun, Jianwei ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CARBON SULFUR BONDS; CARBONYL COMPOUNDS; CHIRAL LIGAND; ENANTIOSELECTIVE; THIOESTERS;

CARBONYLATION; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; NUCLEOPHILES; OXYGEN; PHOSPHORUS COMPOUNDS; SULFUR; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CATALYSTS;

CARBON; CARBONYL DERIVATIVE; GAMMA THIOESTER; LIGAND; NITROGEN; NUCLEOPHILE; OXYGEN; PHOSPHINE; SULFUR; THIOESTER; THIOL; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; POSITION;

CARBON; CATALYSIS; ESTERS; MOLECULAR STRUCTURE; PHOSPHINES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; SULFUR;

EID: 77950852725     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja101251d     Document Type: Article

References (27)

1. For some leading references, see: Sulphur-Containing Drugs and Related Organic Compounds; Damani, L. A., Ed.; Wiley: New York, 1989. Organosulfur Chemistry in Asymmetric Synthesis; Toru, T. and Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 2008. Chiral Sulfur Ligands: Asymmetric Catalysis; Pellissier, H., Ed.; Royal Society of Chemistry: Cambridge, U.K., 2009.
2. For a recent review, see: Enders, D., Lüttgen, K., and Narine, A. A. Synthesis 2007, 959 For a recent example, see
3. Liu, Y., Sun, B., Wang, B., Wakem, M., and Deng, L. J. Am. Chem. Soc. 2009, 131, 418
4. For a pioneering study, see: Marigo, M., Wabnitz, T. C., Fielenbach, D., and Jrgensen, K. A. Angew. Chem., Int. Ed. 2005, 44, 794
5. For a catalytic asymmetric method for the addition of nitrogen at the γ position of aldehydes, see: Bertelsen, S., Marigo, M., Brandes, S., Diner, P., and Jrgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973
6. For some examples of the use of carbon nucleophiles, see: Trost, B. M. and Li, C.-J. J. Am. Chem. Soc. 1994, 116, 3167
7. Zhang, C. and Lu, X. Synlett 1995, 645
8. Chen, Z., Zhu, G., Jiang, Q., Xiao, D., Cao, P., and Zhang, X. J. Org. Chem. 1998, 63, 5631
9. Smith, S. W. and Fu, G. C. J. Am. Chem. Soc. 2009, 131, 14231
10. For some examples of the use of nitrogen nucleophiles, see: Trost, B. M. and Dake, G. R. J. Org. Chem. 1997, 62, 5670
11. Liu, B., Davis, R., Joshi, B., and Reynolds, D. W. J. Org. Chem. 2002, 67, 4595
12. Lu, C. and Lu, X. Org. Lett. 2002, 4, 4677
13. For some examples of the use of oxygen nucleophiles, see: Trost, B. M. and Li, C.-J. J. Am. Chem. Soc. 1994, 116, 10819 Reference 5b
14. Alvarez-Ibarra, C., Csaky, A. G., and de la Oliva, C. G. Tetrahedron Lett. 1999, 40, 8465
15. Chung, Y. K. and Fu, G. C. Angew. Chem., Int. Ed. 2009, 48, 2225
16. For a review of catalytic enantioselective reactions of allenoates, see: Cowen, B. J. and Miller, S. J. Chem. Soc. Rev. 2009, 38, 3102
17. For previous studies of catalytic enantioselective γ additions to allenoates/alkynoates wherein a γ stereocenter is produced, see refs 5d and 7d.
18. For an investigation of catalytic enantioselective γ additions to allenoates/alkynoates with control of the stereochemistry of the - carbon, see ref 5c.
19. For a discussion of the difficulty in synthesizing this family of products, their utility, and an alternative route for their synthesis from triazolyated thiols, see: Armstrong, A., Challinor, L., and Moir, J. H. Angew. Chem., Int. Ed. 2007, 46, 5369
20. Allenoates are readily formed by treating acid chlorides with Wittig reagents.
21. Tang, W. and Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612
22. The potential benefit of additives such as carboxylic acids is described in the initial report by Trost. (5a)
23. For reviews and leading references on nucleophilic catalysis by phosphines, see: Methot, J. L. and Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
24. Ye, L.-W., Zhou, J., and Tang, Y. Chem. Soc. Rev. 2008, 37, 1140
25. Lu, X., Zhang, C., and Xu, Z. Acc. Chem. Res. 2001, 34, 535
26. For a review of enantioselective catalysis by chiral phosphines, see: Marinetti, A. and Voituriez, A. Synlett 2010, 174
27. 31P NMR spectroscopy. The bis(phosphine oxide) is not an effective catalyst for γ additions of thiols to allenoates. In an initial investigation, γ additions of ArSH proceeded in low yields under our standard conditions. Preliminary studies with truncated (monophosphine) relatives of TangPhos furnished little of the γ-addition product.