Copper(I)-fesulphos Lewis acid catalysts for enantioselective Mannich-type reaction of N-sulfonyl imines

Organic Letters

Volumn 8, Issue 14, 2006, Pages 2977-2980

  González, Alvaro Salvador ^a   Arrayás, Ramón Gómez ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746649502     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060866v     Document Type: Article

References (56)

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42. 4 occurs mainly by a stepwise process: initial Mannich-type addition followed by in situ acid-catalyzed cyclization to the formal aza Diels-Alder adduct.
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49. See Supporting Information for details.
50. DCE provided similar results, whereas toluene led to lower yields and enantioselectivities. The use of coordinating solvents such as THF or DMF resulted in no reaction.
51. Lower temperature (0 °C) led to unpractical conversions.
52. The recrystallization yields were typically in the range of 70-90%.
53. Further confirmation of the superiority of N-(2-thienyl)sulfonyl imines over the N-tosyl derivatives resulted from the comparative reaction of 3 with the naphthyl imine 11e and its N-tosyl derivative 11c. Thus, while imine 11e led to the addition product 22e with 71% yield and 91% ee (Table 2, entry 8), 11c afforded 22c in 36% yield and 81% ee.
54. Unfortunately, this N-deprotection method is not suitable for ketone derivatives. For example, complete disappearance of starting material was observed upon treatment of compounds 30e and 31e with Mg in MeOH for 4 h, but only decomposition products were detected in the reaction mixture.
55. These reductive reaction conditions had been reported for the cleavage of 2-pyridylsulfonyl-protected amines: Pak, C. S.; Lim, D. S. Synth. Commun. 2001, 2209.
56. Hata, S.; Iguchi, M.; Iwasawa, T.; Yamada, K.-i.; Tomioka, K. Org. Lett. 2004, 6, 1721.