✦ LIBER ✦

Stereoselective synthesis of CF3-substituted aziridines by Lewis acid-mediated aziridination of aldimines with diazoacetates

✍ Scribed by Takahiko Akiyama; Satoshi Ogi; Kohei Fuchibe

Book ID: 104253607
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 202 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00854-2

No coin nor oath required. For personal study only.

✦ Synopsis

Treatment of trifluoroacetaldehyde N,O-acetal with diazoacetate in the presence of a Lewis acid furnished CF 3 -substituted aziridinecarboxylates in good yields. Both cis and trans isomers were obtained stereoselectively by the proper choice of the ester substituents. Use of a chiral diazoacetate derived from (R)-pantolactone led to highly diastereoselective aziridination (94% de).

📜 SIMILAR VOLUMES

Stereoselective Synthesis of CF3-Substit

Stereoselective Synthesis of CF3-Substituted Aziridines by Lewis Acid Mediated Aziridination of Aldimines with Diazoacetates.

✍ Takahiko Akiyama; Satoshi Ogi; Kohei Fuchibe 📂 Article 📅 2003 🏛 John Wiley and Sons ⚖ 149 KB 👁 2 views

InCl3 catalyzed reactions of ethyl diazo

InCl3 catalyzed reactions of ethyl diazoacetate with aldimines: a highly diastereoselective synthesis of cis-aziridine carboxylates

✍ Saumitra Sengupta; Somnath Mondal 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 139 KB

InCl 3 catalyzed reactions of ethyl diazoacetate with aldimines give aziridine carboxylates under mild conditions, low catalyst loading and with high cis-selectivity.

ChemInform Abstract: Lewis Acid Promoted

ChemInform Abstract: Lewis Acid Promoted Aziridination of Imines with Semistabilized Sulfonium Ylides: Highly Stereoselective Synthesis of Vinyl- and Ethynyl-Aziridines.

✍ D.-K. WANG; L.-X. DAI; X.-L. HOU 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

ChemInform Abstract: InCl3-Catalyzed Rea

ChemInform Abstract: InCl3-Catalyzed Reactions of Ethyl Diazoacetate with Aldimines: A Highly Diastereoselective Synthesis of cis-Aziridine Carboxylates.

✍ Saumitra Sengupta; Somnath Mondal 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 29 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Lewis Acid Promoted Regio- and Stereosel

Lewis Acid Promoted Regio- and Stereoselective Hetero Nucleophilic Addition to a Piperidinyl Aziridine. Synthesis of trans 3-Amino-4-substituted Piperidines.

✍ X. Eric Hu 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 2 views

Lewis acid promoted regio- and stereosel

Lewis acid promoted regio- and stereoselective hetero nucleophilic addition to a piperidinyl aziridine. Synthesis of trans 3-amino-4-substituted piperidines

✍ X.Eric Hu 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 117 KB

A piperidinyl aziridine underwent alcoholic nucleophilic addition with alcohols to result in corresponding trans 3-amino-4-substituted piperidines. The addition reaction was catalyzed by BF 3 •OEt 2 in excellent regio-and stereoselectivity. The application of this method was extended to the addition