Catalytic asymmetric direct-type 1,4-addition reactions of simple esters‡
Literature Information
Publication Date
2016-06-29
DOI
10.1039/C6QO00242K
Impact Factor
5.281
Authors
Io Sato, Hirotsugu Suzuki, Yasuhiro Yamashita, Shū Kobayashi
View Original
Abstract
In the presence of catalytic amounts of potassium hexamethyldisilazide (KHMDS) and a chiral macrocyclic crown ether, asymmetric 1,4-addition reactions of simple esters with α,β-unsaturated amides proceeded to afford the desired 1,4-adducts in high yields with good stereoselectivities. Mechanistic investigations revealed that proper combination of substrates was a key for the efficient catalytic turnover.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine
CAS Number:
29216-28-2
Molecular Formula:
C20H22N2S
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