Chiral Lithium Amides as Key Reagents in Enantioselective Synthesis of 2-Alkylpyridines with Multiple Stereocenters

A direct enantioselective conjugate addition of 2-alkylpyridines enables efficient construction of complex functionalized pyridinyl scaffolds with contiguous stereocenters. This method leverages chiral lithium amides as traceless stereodirecting auxiliaries, operating through defined aggregation of organolithium intermediates to achieve excellent enantio- and diastereocontrol.

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Publication Details

Journal
Journal of the American Chemical Society
Published
2025-10-15
DOI
https://doi.org/10.1021/jacs.5c13977
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
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article

Chiral Lithium Amides as Key Reagents in Enantioselective Synthesis of 2-Alkylpyridines with Multiple Stereocenters

Leroy Lu, Armen Zakarian, Priya Kandiyal, Dyllan P. Ly
Journal of the American Chemical Society
Advanced Synthetic Organic Chemistry
article

Chiral Lithium Amides as Key Reagents in Enantioselective Synthesis of 2-Alkylpyridines with Multiple Stereocenters

Leroy Lu, Armen Zakarian, Priya Kandiyal, Dyllan P. Ly
article en

Abstract

A direct enantioselective conjugate addition of 2-alkylpyridines enables efficient construction of complex functionalized pyridinyl scaffolds with contiguous stereocenters. This method leverages chiral lithium amides as traceless stereodirecting auxiliaries, operating through defined aggregation of organolithium intermediates to achieve excellent enantio- and diastereocontrol.

Journal of the American Chemical SocietyVol. 147(43)
University of California, Santa Barbara (US), University of California System (US)
Openalex Percentile: Top 78%
Advanced Synthetic Organic Chemistry
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