Boiling water-catalyzed neutral and selective N-Boc deprotection.
نویسندگان
چکیده
A general protocol for removing Boc groups from various types of nitrogen is reported and a preliminary investigation of the reaction mechanism indicates that water acts as a dual acid/base catalyst at elevated temperature.
منابع مشابه
Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N-Boc imines and nitroalkenes.
A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.
متن کاملA Novel Access to Tertiary and Secondary or^o-Aminophenylphosphines by Protected Group Synthesis and Palladium Catalyzed P-C Coupling Reactions
tert-Butoxycarbonylaniline, orf/zo-Lithiation, Chlorophosphines The dilithium salt la formed by ortho-metallation of N-terf-butoxycarbonylaniline (BOCaniline) 1 with two equivalents of ter/-butyllithium reacts with the chlorophosphines Ph3_„PCl„ (n = 1 3) to yield the BOC protected ort/zo-aminophenylphosphines 2 4 in high yields. On deprotection of 2 4 with trimethylchlorosilane in the presence...
متن کاملCombining the benefits of homogeneous and heterogeneous catalysis with tunable solvents and nearcritical water.
The greatest advantage of heterogeneous catalysis is the ease of separation, while the disadvantages are often limited activity and selectivity. We report solvents that use tunable phase behavior to achieve homogeneous catalysis with ease of separation. Tunable solvents are homogeneous mixtures of water or polyethylene glycol with organics such as acetonitrile, dioxane, and THF that can be used...
متن کاملAn Expedient Total Synthesis of Triciribine.
In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) gro...
متن کاملAsymmetric, anti-selective scandium-catalyzed Sakurai additions to glyoxyamide. Applications to the syntheses of N-boc D-alloisoleucine and D-isoleucine.
[reaction: see text] An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-Boc D-alloisoleucine and D-isoleucine are described.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 34 شماره
صفحات -
تاریخ انتشار 2009