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Synfacts 2014; 10(5): 0498
DOI: 10.1055/s-0033-1341145
DOI: 10.1055/s-0033-1341145
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Synthesis of β2,2-Amino Acids via Asymmetric Friedel–Crafts Alkylation
Weng J.-Q, Deng Q.-M, Wu L, Xu K, Wu H, Liu R.-R, Gao J.-R, Jia Y.-X * Zhejiang University of Technology, Hangzhou, P. R. of China
Asymmetric Friedel–Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters.
Org. Lett. 2014;
16: 776-779
Asymmetric Friedel–Crafts Alkylation of α-Substituted β-Nitroacrylates: Access to β2,2-Amino Acids Bearing Indolic All-Carbon Quaternary Stereocenters.
Org. Lett. 2014;
16: 776-779
Further Information
Publication History
Publication Date:
17 April 2014 (online)
Significance
Jia and co-workers report the nickel-catalyzed asymmetric Friedel–Crafts alkylation of α-substituted β-nitroacrylates. A series of chiral indolic β-nitroesters bearing all-carbon quaternary stereocenters were prepared in excellent yields (up to 98%) with excellent enantioselectivities (up to 97% ee).
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Comment
The authors have developed a highly enantioselective Michael-type Friedel–Crafts alkylation of indoles. One of the products was readily converted into a chiral tryptophan-type β2,2-amino ester and tetrahydro-β-carboline through nitro reduction and sequential Pictet–Spengler cyclization.
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