[3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates

Tetrahedron Letters

Volumn 44, Issue 27, 2003, Pages 5033-5035

  Jao, Edwin ^a   Bogen, Stephane ^a   Saksena, Anil K ^a   Girijavallabhan, Viyyoor ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; GAMMA LACTAM DERIVATIVE; PROLINE DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; PYROGLUTAMINOL; TOLUENE; UNCLASSIFIED DRUG; [2 (ACETOXYMETHYL) 3 ALLYL]TRIMETHYLSILANE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0037842854     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01191-2     Document Type: Article

References (15)

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3. For some reviews, see: (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1; (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49; For an example where TMM entity is incorporated into a five-membered ring, see: (c) Romero, J. M. L.; Sapmaz, S.; Fensterbank, L.; Malacria, M. Eur. J. Org. Chem. 2001, 767-773.
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9. 3).
10. 2 (M+H)=256.1338, found 256.1340.
11. 3 (1.6 equiv., 138 mmol, 28.70 g). The mixture was refluxed for 13 h, cooled down then directly loaded on a Biotage 75M (400 g Silica) cartridge. Flash chromatography (30 to 100% EtOAc-hexane) afforded 2 (17.34 g, 80% yield) as a colorless oil.
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14. Work-up was carried out following Micovic's procedure. See: Micovic V.M., Mihailovic M.L.J. J. Org. Chem. 18:1953;1190.
15. D=-16.4° (c 0.9, MeOH).