Ag(I)-Fesulphos-Catalyzed Enantioselective Synthesis of 3‑Silylproline Derivatives

An efficient catalytic asymmetric 1,3-dipolar cycloaddition of N-benzylidineiminoglycinate-derived azomethine ylides to β-silylmethylene malonates catalyzed by a Ag­(I)-Fesulphos complex has been developed, affording fully substituted 3-silylproline derivatives with an all carbon quaternary center....

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Bibliographic Details
Published in:Journal of organic chemistry 2019-03, Vol.84 (5), p.2404-2414
Main Authors: Chowdhury, Raghunath, Dubey, Akhil K, Ghosh, Sunil K
Format: Article
Language:English
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Summary:An efficient catalytic asymmetric 1,3-dipolar cycloaddition of N-benzylidineiminoglycinate-derived azomethine ylides to β-silylmethylene malonates catalyzed by a Ag­(I)-Fesulphos complex has been developed, affording fully substituted 3-silylproline derivatives with an all carbon quaternary center. The silylproline derivatives were obtained in moderate-to-good yields (up to 81%) in high diastereoselectivities and enantioselectivities (dr up to 95:5; er up to 96:4). Tamao–Fleming oxidation of selected 3-silylproline derivatives provided not only an efficient route but also the shortest route to 3-hydroxyproline derivatives, which are not accessible by direct 1,3-dipolar cycloadditions of azomethine ylide with frequently used arylidene/alkylidene malonates.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02412