TY - JOUR
T1 - Nucleophilic and Electrophilic Activation of Non-Heteroaromatic Amides in Atom-Economical Asymmetric Catalysis
AU - Kumagai, Naoya
AU - Shibasaki, Masakatsu
N1 - Funding Information:
The authors thank JST, ACT-C (for M.S.), and JSPS KAKENHI (grant no. 25713002; for N.K.) for financial support. JSPS KAKENHI grant number 16H01043 in Precisely Designed Catalysts with Customized Scaffolding (for N.K.) is also acknowledged.
Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/10/17
Y1 - 2016/10/17
N2 - Recent advances in catalytic asymmetric carbon–carbon bond-forming reactions of non-heteroaromatic amide substrates are highlighted. Among carbonyl compounds, amides have received limited attention in catalytic asymmetric transformations mainly owing to their lower reactivity. Amides are reluctant to form enolates for nucleophilic addition, and α,β-unsaturated amides exhibit diminished electrophilicity at the β-carbon. Recent advances in asymmetric catalysis rendered these amides amenable to enantioselective reactions with perfect atom economy, producing synthetically useful chiral building blocks. This Minireview summarizes recent developments in the field.
AB - Recent advances in catalytic asymmetric carbon–carbon bond-forming reactions of non-heteroaromatic amide substrates are highlighted. Among carbonyl compounds, amides have received limited attention in catalytic asymmetric transformations mainly owing to their lower reactivity. Amides are reluctant to form enolates for nucleophilic addition, and α,β-unsaturated amides exhibit diminished electrophilicity at the β-carbon. Recent advances in asymmetric catalysis rendered these amides amenable to enantioselective reactions with perfect atom economy, producing synthetically useful chiral building blocks. This Minireview summarizes recent developments in the field.
KW - C−C coupling
KW - amides
KW - asymmetric catalysis
KW - atom economy
KW - synthetic methods
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U2 - 10.1002/chem.201602484
DO - 10.1002/chem.201602484
M3 - Review article
AN - SCOPUS:84990197293
SN - 0947-6539
VL - 22
SP - 15192
EP - 15200
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 43
ER -