Desymmetrizing asymmetric ring expansion: stereoselective synthesis of 7-membered cyclic β-keto carbonyl compounds with an α-hydrogen

2010 ◽  
Vol 46 (36) ◽  
pp. 6810 ◽  
Author(s):  
Takuya Hashimoto ◽  
Yuki Naganawa ◽  
Keiji Maruoka
Keyword(s):  
Carbonyl Compounds ◽  
Stereoselective Synthesis ◽  
Ring Expansion

Fluorinative Ring-Expansion of Cyclic Ethers Using p-Iodotoluene Difluoride. Stereoselective Synthesis of Fluoro Cyclic Ethers.

ChemInform ◽  
2003 ◽  
Vol 34 (33) ◽  
Author(s):  
Tomotake Inagaki ◽  
Yutaka Nakamura ◽  
Masanori Sawaguchi ◽  
Norihiko Yoneda ◽  
Shinichi Ayuba ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Ring Expansion ◽  
Cyclic Ethers

Reaction of dimethoxycarbene with strained cyclic carbonyl compounds

2000 ◽  
Vol 78 (9) ◽  
pp. 1194-1203
Author(s):  
Paul C Venneri ◽  
John Warkentin
Keyword(s):  
Carbonyl Group ◽  
Carbonyl Compounds ◽  
Ring Expansion ◽  
Carbonyl Groups

A cyclopropanone, a cyclopropenone, cyclobutanones, a cyclobutane-1,3-dione, and a cyclobutene-1,2-dione reacted with dimethoxycarbene to afford acetals of the next larger ring by formal insertion of the carbene into a C—C bond α to the carbonyl group. When either of two saturated α-ring carbons could be involved in the process, the ring expansion was selective, affording primarily the product of apparent insertion into the more substituted ring bond. With 2,3-dimethoxycyclobutene-1,2-dione, insertion occurred between the carbonyl groups and with β-propiolactone it occurred at the lactone bond. β-Propiolactam, however, reacted by insertion of the carbene into the N—H bond.Key words: β-propiolactone, cyclobutanone, cyclobutananedione, cyclopropanone, dialkoxycarbene.

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