Stereoselective Ring Opening of meso Bicyclic Hydrazines: A Straightforward Approach to Hydrazino Cyclopentenic Cores

Organic Letters

Volumn 5, Issue 25, 2003, Pages 4771-4774

  Pérez Luna, Alejandro ^a   Cesario, Michèle ^b   Bonin, Martine ^a   Micouin, Laurent ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALLYL COMPOUND; BICYCLO COMPOUND; CYCLOPENTENE DERIVATIVE; HYDRAZINE DERIVATIVE; LIGAND; PALLADIUM;

ARTICLE; CATALYSIS; CHIRALITY; DIELS ALDER REACTION; ENANTIOMER; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0347683362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0357393     Document Type: Article

References (34)

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29. From allylic aziridines: Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. From azabicyclic substrates: (a) Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 2, 1580. Other metal-catalyzed enantioselective ring openings of azabicyclic derivatives have also been described, but consideration of their stereo- and regioselectivity led the authors to propose a mechanism not involving π-allyl species: (b) Lautens, M.; Hiebert, S.; Renaud, J.-L. Org. Lett. 2000, 2, 1971. (c) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
30. From allylic aziridines: Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433. From azabicyclic substrates: (a) Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 2, 1580. Other metal-catalyzed enantioselective ring openings of azabicyclic derivatives have also been described, but consideration of their stereo- and regioselectivity led the authors to propose a mechanism not involving π-allyl species: (b) Lautens, M.; Hiebert, S.; Renaud, J.-L. Org. Lett. 2000, 2, 1971. (c) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
31. dppf: 1,1′-bis-(diphenylphosphino)ferrocene.
32. 2 (2.3 mg, 0.0063 mmol) and 1,1′-bis-(diphenylphosphino)-ferrocene (9.5 mg, 0.017 mmol) were placed in a Schlenk tube, dried under vacuum (0.1 mmHg) for 1 h, and then placed under argon. Freshly distilled THF (3 mL) was degassed and then added to the mixture at room temperature. The yellow solution was stirred for 30 min. 4 (96 mg, 0.26 mmol) and phenol (127.5 mg, 1.35 mmol) dissolved in THF (1 mL) were added. Next, NaH (60% dispersion in mineral oil, 8.1 mg, 0.2 mmol) was added and the solution was stirred at room temperature until TLC analysis indicated full conversion. After dilution with diethyl ether (5 mL), the mixture was washed with sodium hydroxide (1 M, 2 x 5 mL) and brine (5 mL) and concentrated. Purification by flash chromatography (cyclohexane/ethyl acetate = gradient) afforded 8a as a slowly crystallizing white solid (100 mg, 83%).
33. See Supporting Information. PHOX: 2-[2(diphenylphosphino)-phenyl]-4- phenyl-4,5-dihydrooxazole. No conversion was obtained when using the classical Trost ligand 1,2-diaminocyclohexane-N,N′-bis(2′-diphenyl- phosphinobenzoyl).
34. Trost, B. M.; Patterson, D. E. J. Org. Chem. 1998, 63, 1339.