TTMPP: An efficient organocatalyst in the ring-opening of aziridines with silylated nucleophiles.
نویسندگان
چکیده
The ring-opening of N-tosylaziridines with silylated nucleophiles catalyzed by tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) afforded the corresponding beta-functionalized sulfonamides in excellent yield under mild reaction conditions.
منابع مشابه
Efficient Regioselective Ring Opening of Activated Aziridine-2-Carboxylates with [18F]Fluoride
Aziridines can undergo a range of ring-opening reactions with nucleophiles. The regio- and stereochemistry of the products depend on the substituents on the aziridine. Aziridine ring-opening reactions have rarely been used in radiosynthesis. Herein we report the ring opening of activated aziridine-2-carboxylates with [(18)F]fluoride. The aziridine was activated for nucleophilic attack by substi...
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tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N-N ylide generated in situ from N-methylmorpholine and O-diphenylphosphinyl hydroxylamine. The resulting N-unfunctionalised aziridines are shown to be versatile synthetic building blocks that undergo highly selective ring-opening reactions with a wide range of nucleophiles.
متن کاملLewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds: further support towards an SN2-type mechanism
A highly regioselective SN2-type ring opening of 2-aryl-N-tosylaziridines with carbonyl compounds in the presence of a Lewis acid to afford various 1,3-oxazolidines and 1,2-amino alcohols in excellent yields and moderate to high enantioselectivity is described. The formation of non-racemic products provides convincing evidence for the SN2-type ring opening mechanism. 2007 Elsevier Ltd. All righ...
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 7 18 شماره
صفحات -
تاریخ انتشار 2009