Highly Enantioselective Mannich Reactions with α-Aryl Silyl Ketene Acetals and Imines

Mannich reactions with chiral silicon Lewis acid activated acylhydrazones and α-aryl silyl ketene acetals and α-aryl,α-alkyl silyl ketene imines proceed efficiently and with good to excellent levels of both diastereoselectivity and enantioselectivity. The reactions provide access to α-aryl,β-hydrazi...

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Bibliographic Details
Published in:Organic letters 2011-02, Vol.13 (4), p.816-818
Main Authors: Notte, Gregory T, Baxter Vu, Jenny M, Leighton, James L
Format: Article
Language:English
Subjects:
Acetals - chemistry
Amino Acids - chemical synthesis
Amino Acids - chemistry
Esters
Ethylenes - chemistry
Imines - chemistry
Ketones - chemistry
Nitriles - chemical synthesis
Nitriles - chemistry
Organosilicon Compounds - chemistry
Stereoisomerism
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Summary:Mannich reactions with chiral silicon Lewis acid activated acylhydrazones and α-aryl silyl ketene acetals and α-aryl,α-alkyl silyl ketene imines proceed efficiently and with good to excellent levels of both diastereoselectivity and enantioselectivity. The reactions provide access to α-aryl,β-hydrazido esters and α-aryl,α-alkyl,β-hydrazido nitriles, which are valuable analogs of β-amino acids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol103096u