BINAP-AgSbF6 vs. BINAP-AgClO4 complexes as catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes

Synlett

Volumn , Issue 6, 2010, Pages 962-966

  Martín Rodríguez, María ^a   Nájera, Carmen ^a   Sansano, José M ^a   Costa, Paulo R R ^b   De Lima, Evanoel Crizanto ^b   Dias, Ayres G ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b Nucleo de Pesq de Produtos Naturais   (Brazil)

Author keywords

Asymmetric catalysis; Azomethine ylides; Multicomponent reaction; Prolines; Silver salts

Indexed keywords

ALKENE DERIVATIVE; AZOMETHINE YLIDE; ETHYLENE; MALEIMIDE DERIVATIVE; TRANS 1,2BIS(PHENYLSULFONYL)ETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 77949894124     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219534     Document Type: Article

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64. The BINAPAgSbF6 (2:1) chiral cluster was not characterized because it afforded lower endo/exo diastereoselectivity, such as occurred in the previously reported chiral BINAPAgClO4-catalyzed 1,3-DC (ref. 7).
65. General Procedure for the Catalytic Enantioselective 1,3-DC Using Silver Salts A solution of the imino ester (1 mmol) and dipolarophile (1 mmol) in toluene (5 mL) was added to a suspension containing (R)- or (S)-BINAP (0.05 mmol, 31 mg) and silver(I) salt (0.05 mmol) in toluene (5 mL). To the resulting suspension Et3N (0.05 mmol, 7 mL) was added and the mixture stirred at r.t. and in the absence of the light for 1648 h (see main text). The reaction was filtered, the organic filtrate was directly evaporated, and the residue was purified by recrystallization or by flash chromatography yielding pure endo cycloadducts. General Procedure for the Three-Component Catalytic Enantioselective 1,3-DC Using Silver Salts To a suspension containing (R)- or (S)-BINAP (0.05 mmol, 31 mg) and AgSbF6 (0.05 mmol, 17 mg) in toluene (10 mL) was added the freshly distilled aldehyde (1 mmol), glycine methyl ester hydrochloride (1 mmol), the dipolarophile (1 mmol), and Et3N (140 mL, 1.05 mmol). The mixture was stirred at r.t. and in the absence of the light for 1648 h (see main text). Following the same workup as that described above, final cycloadducts 3aa and 8c were obtained.