Electroorganic chemistry. 124. Electroreductive intramolecular coupling of. alpha.-(. omega.-bromoalkyl). beta.-keto esters

T Shono, N Kise, N Uematsu, S Morimoto…

Index: Shono, Tatsuya; Kise, Naoki; Uematsu, Nobuyuki; Morimoto, Shinji; Okazaki, Eiichi Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5037 - 5041

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Citation Number: 23

Abstract

Intramolecular coupling occurs when cyclic a-(bromomethyl)@-keto esters are electrochemically reduced in the presence of trimethylsilyl chloride and one-carbon ring- enlarged products are obtained in reasonable yields. Electroreduction of a-(7-bromopropyl) &keto esters also affords the corresponding five-membered cyclized products and/or the corresponding ring-opened compounds. The ease of ring opening of the cyclized products ...

~4%

~17%

~80%

~83%

~51%

Diastereoselectivity Control of the Radical Carboazidation o...

[Cren, Sylvaine; Schar, Pascal; Renaud, Philippe; Schenk, Kurt Journal of Organic Chemistry, 2009 , vol. 74, # 8 p. 2942 - 2946]

Novel free radical ring-expansion reactions

[Dowd, Paul; Choi, Soo-Chang Tetrahedron, 1989 , vol. 45, # 1 p. 77 - 90]

Studies on diastereoselective reduction of cyclic β-ketoeste...

[Fraga, Carlos A.M.; Teixeira, Lis Helena P.; Menezes, Carla Maria De S.; Sant'Anna, Carlos Mauricio R.; Ramos, Maria Da Conceicao K.V.; De Aquino Neto, Francisco R.; Barreiro, Eliezer J. Tetrahedron, 2004 , vol. 60, # 12 p. 2745 - 2755]

Novel free radical ring-expansion reactions

[Dowd, Paul; Choi, Soo-Chang Tetrahedron, 1989 , vol. 45, # 1 p. 77 - 90]