Mild Approach to the Deprotection of Troc from Protected Amines Using Mischmetal and TMSCl

REFERENCES

• Doi , T. ; Numajiri , Y. ; Munakata , A. ; Takahashi , T. Total synthesis of apratoxin A . Org. Lett. 2006 , 8 , 531 – 534 .
   PubMed Web of Science ®Google Scholar
• Hayashi , Y. ; Skwarczynski , M. ; Hamada , Y. ; Sohma , Y. ; Kimura , T. ; Kiso , Y. A. Novel approach of water-soluble paclitaxel prodrug with no auxiliary and no byproduct: Design and synthesis of isotaxel . J. Med. Chem. 2003 , 46 , 3782 – 3784 .
   PubMed Web of Science ®Google Scholar
• Zeghida , W. ; Demeunynck , M. Application of 2,2,2-trichloroethoxycarbonyl protection to aminoacridines . Synthesis 2007 , 231 – 207 .
   Google Scholar
• Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis ; John Wiley and Sons : New York , 1999 .
   Google Scholar
• Mäeorg , U. ; Ragnarsson , U. Synthesis, application, and scope of a new protected hydrazine reagent . Tetrahedron Lett. 1998 , 39 , 681 – 684 .
   Google Scholar
• Woodward , R. B. ; Heusler , K. ; Gosteli , J. ; Naegeli , P. ; Oppolzer , W. ; Ramage , R. ; Ranganathan , S. ; Vorbrüggen , H. The total synthesis of cephalosporin C1 . J. Am. Chem. Soc. 1966 , 88 , 852 – 853 .
   Web of Science ®Google Scholar
• Mineno , T. ; Choi , S. R. M. ; Avery , A. A mild deprotection of trichloroethyl carbamates using indium metal. Synlett 2002, 883–886.
   Web of Science ®Google Scholar
• Tokimoto , H. ; Fukase , K. New deprotection method of the 2,2,2-trichloroethoxycarbonyl (Troc) group with (Bu3Sn)2 . Tetrahedron Lett. 2005 , 46 , 6831 – 6832 , and references therein.
   Web of Science ®Google Scholar
• Somsak , L. ; Czifrak , K. ; Veres , E. Selective removal of 2,2,2-trichloroethyl- and 2,2,2-trichloroethoxycarbonyl protecting groups with Zn–N-methylimidazole in the presence of reducible and acid-sensitive functionalities . Tetrahedron Lett. 2004 , 45 , 9095 – 9097 .
   Google Scholar
• Vellemäe , E. ; Lebedev , O. ; Sillard , R. ; Mäeorg , U. A selective method for cleavage of N-Troc-protected hydrazines and amines under mild conditions using mischmetal and TMSCl . J. Chem. Res. 2006 , 11 , 685 – 687 .
   Google Scholar
• Mäeorg , U. ; Pehk , T. ; Ragnarsson , U. Synthesis of substituted hydrazines from triprotected precursors . Acta Chem. Scand. 1999 , 53 , 1127 – 1133 .
   Google Scholar
• Stafford , J. A. ; Brackeen , M. F. ; Karanewsky , D. S. ; Valvano , N. L. A highly selective protocol for the deprotection of Boc-protected amides and carbamates . Tetrahedron Lett. 1993 , 34 , 7873 – 7876 .
   Google Scholar
• Betancourt , J. M. ; Martin , T. ; Palazon , J. M. ; Martin , V. S. Stereoselective synthesis of cyclic ethers by intramolecular trapping of dicobalt hexacarbonyl-stabilized propargylic cations . J. Org. Chem. 2003 , 68 , 3216 – 3224 .
   PubMedGoogle Scholar
• Yun-Fei , D. ; Yu-Qing , C. ; Zhi , D. ; Bao-Hua , C. A study on the heterogeneous reaction of trialkylsilyl chlorides with inorganic salts and monocarboxylates catalyzed by PEG 400 . J. Chem. Res. 2004 , 3 , 223 – 225 .
   Google Scholar
• Mormann , W. ; Leukel , G. A simple and versatile synthesis of trimethylsiloxy-substituted isocyanates . Synthesis 1988 , 990 – 992 .
   Google Scholar
• Lebel , H. ; Huard , K. De novo synthesis of Troc-protected amines: Intermolecular rhodium-catalyzed C-H amination with N-tosyloxycarbamates . Org. Lett. 2007 , 9 , 639 – 642 .
   PubMed Web of Science ®Google Scholar
• Kober , R. ; Steglich , W. Reaction of acylaminobromomalonates and acylaminobromoacetates with trialkyl phosphites—a simple synthesis of ethyl 2-amino-2-(diethoxyphosphoryl)acetate . Liebigs Ann. Chem. 1983 , 4 , 599 – 609 .
   Google Scholar
• Shimizu , M. ; Sodeoka , M. Convenient method for the preparation of carbamates, carbonates, and thiocarbonates . Org. Lett. 2007 , 9 , 5231 .
   PubMed Web of Science ®Google Scholar
• Pek , Y. ; Chong , P. Y. ; Janicki , S. Z. ; Petillo , P. A. Multilevel selectivity in the mild and high-yielding chlorosilane-induced cleavage of carbamates to isocyanates . J. Org. Chem. 1998 , 63 , 8515 – 8521 .
   Google Scholar