Enantioselective construction of spirocyclic oxindolic cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition

Journal of the American Chemical Society

Volumn 129, Issue 41, 2007, Pages 12396-12397

  Trost, Barry M ^a   Cramer, Nicolai ^a   Silverman, Steven M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; CYCLOPROPANE; PALLADIUM; SPIRO COMPOUND; TRIMETHYLENEMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

CATALYSIS; CYCLIZATION; INDOLES; MACROCYCLIC COMPOUNDS; METHANE; METHYLATION; MOLECULAR STRUCTURE; PALLADIUM; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 35348943329     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075335w     Document Type: Article

References (17)

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2. (a) Trost, B. M. Angew. Chem., Int. Ed. 1986, 25, 1.
3. (b) Trost, B. M. Pure Appl. Chem. 1988, 60, 1615.
4. (c) Chan, D. T. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A.; Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 57-84 and references cited therein.
5. (a) Trost, B. M.; Stambuli, J. P.; Silverman, S. M.; Schwörer, U. J. Am. Chem. Soc. 2006, 128, 13328.
6. (b) Yamamoto, A.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 375.
7. Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086.
8. Trost, B. M.; Nanninga, T. N.; Satoh, T. J. Am. Chem. Soc. 1985, 107, 721.
9. Gordon, D. J.; Fenske, R. F.; Nanninga, T. N.; Trost, B. M. J. Am. Chem. Soc. 1981, 103, 5974.
10. The parent unsubstituted TMM-donor gave under identical reaction conditions a quantitative yield and 71% ee with L2.
11. Trost, B. M.; Silverman, S. M.; Stambuli, J. P. J. Am. Chem. Soc., in press.
12. Partial equilibration of the double bond prior to the cycloaddition occurs when using the more nucleophilic HMPT as ligand.
13. With this substrate class, a scrambling of the double-bond geometry through bond rotation of an intermediate species is not observed, which is in accordance with both a stepwise mechanism and fast ring closure (Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1980, 102, 6359.
14. Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1983, 105, 2326.)
15. or a concerted mechanism described by Singleton (Singleton, D. A.; Schulmeier, B. E. J. Am. Chem. Soc. 1999, 121, 9313).
16. Double bond migration of preferentially one product isomer occurred.
17. Peterson, E. A.; Overman, L. E. Proc Natl Acad Sci U.S.A. 2004, 101, 11943.