The Journal of Organic Chemistry

Selective transformation of O-2-(trimethylsilyl) ethyl and O-tert-butyl carbamates into O-benzyl carbamates using benzyl trichloroacetimidate

AGM Barrett, D Pilipauskas

Index: Barrett, Anthony G. M.; Pilipauskas, Daniel Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5170 - 5173

Full Text: HTML

Citation Number: 19

Abstract

I tively, when R2 is a 2-(trimethylsily1) ethyl group, SN1 fragmentation and subsequent nucleophilic attack at sil-icon by the trichloroacetamide gives the product carbamate, ethylene, and the positively charged TMS adduct. However, when R2 is a methyl group, cleavage of the cation occurs presumably via debenzylation with the formation of N- benzyltrichloroacetamide rather than de-0-methylation with formation of the benzyl ...

Related Articles:

Synthesis of N-Methyl L-Phenylalanine for Total Synthesis of Pepticinnamin E

[Sun, Dequn; Zhang, Lingzi; Wang, Jin Asian Journal of Chemistry, 2012 , vol. 24, # 1 p. 319 - 322]

Synthesis of carbamates using yttria-zirconia based Lewis acid catalyst

[Pandey, Rajesh K.; Dagade, Sharda P.; Dongare, Mohan K.; Kumar, Pradeep Synthetic Communications, 2003 , vol. 33, # 23 p. 4019 - 4027]

Pd/C (en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations

[Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku Tetrahedron, 2000 , vol. 56, # 43 p. 8433 - 8441]

Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates

[Sakaitani, Masahiro; Ohfune, Yasufumi Journal of Organic Chemistry, 1990 , vol. 55, # 3 p. 870 - 876]

Palladium catalyzed reductive deprotection of Alloc: Transprotection and peptide bond formation

[Beugelmans, Rene; Neuville, Luc; Bois-Choussy, Michele; Chastanet, Jacqueline; Zhu, Jieping Tetrahedron Letters, 1995 , vol. 36, # 18 p. 3129 - 3132]

More Articles...