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DOI: 10.1055/s-0029-1219534
BINAP-AgSbF6 vs. BINAP-AgClO4 Complexes as Catalysts for the Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes
Publication History
Publication Date:
23 February 2010 (online)
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Abstract
The employment of AgSbF6 and BINAP ligands has been evaluated in the catalyzed enantioselective 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes. The results are compared with the analogous ones obtained when using AgClO4. The cycloaddition with maleimides and trans-1,2-bis(phenylsulfonyl)ethylene are clearly improved by the AgSbF6-derived catalyst, and its efficiency is crucial for ensure good yields and excellent ee in the three-component reaction.
Key words
asymmetric catalysis - prolines - silver salts - azomethine ylides - multicomponent reaction
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References and Notes
The BINAP-AgSbF6 (2:1) chiral cluster was not characterized because it afforded lower endo/exo diastereoselectivity, such as occurred in the previously reported chiral BINAP-AgClO4-catalyzed 1,3-DC (ref. 7).
16
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 µL)
was added and the mixture stirred at r.t. and in the absence of
the light for 16-48 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 µL, 1.05 mmol). The mixture was stirred at r.t. and
in the absence of the light for 16-48 h (see main text).
Following the same workup as that described above, final cycloadducts 3aa and 8c were
obtained.