Unexplored nucleophilic ring opening of aziridines.

نویسندگان

  • Ana María Costero
  • Salvador Gil
  • Margarita Parra
  • Pablo Rodríguez
چکیده

The reactivity of dianions of carboxylic acids towards aziridines has been studied. Although, a similar reactivity to that of enolates from ketones, esters or amides has been observed, the method directly yields γ-aminoacids in one step. The method is complementary of previous results of enenediolate reactivity with other electrophiles. A comparative study with the reactivity of this enediolates with epoxides is included.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Lewis 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...

متن کامل

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...

متن کامل

Ring-opening reaction of Bus- and SES-protected aziridines using lithiated dithianes.

The scope and limitation of the ring-opening reaction of sulfonyl-activated aziridines using lithiated dithianes was investigated. Nucleophilic attack of lithiated dithianes on aziridines containing tert-butylsulfonyl (Bus) and 2-(trimethylsilyl)ethylsulfonyl (SES) demonstrated efficient ring cleavage to yield beta-amino carbonyl equivalents, gamma-lactam and syn- and anti-1,5-aminoalcohols. Th...

متن کامل

Mild metal-free syn-stereoselective ring opening of activated epoxides and aziridines with aryl borates.

A conceptually new, simple and practical method for the syn-nucleophilic displacement of aryl and vinyl epoxides and aryl aziridines with (substituted) phenols, using aryl borates as activating nucleophiles under neutral conditions, is reported.

متن کامل

A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors

A hydrogen polysulfide mediated aziridine ring-opening reaction was discovered. Based on this reaction, a novel H2S(n)-specific chemosensor (AP) was developed. AP showed high sensitivity and selectivity for H2S(n). Notably, the fluorescent turn-on product (1) exhibited excellent two-photon photophysical properties, a large Stokes shift, and high solid state luminescent efficiency.

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Molecules

دوره 15 12  شماره 

صفحات  -

تاریخ انتشار 2010