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Literature DB >> 23687986

Isotope effects and mechanism of the asymmetric BOROX Brønsted acid catalyzed aziridination reaction.

Mathew J Vetticatt¹, Aman A Desai, William D Wulff.

Abstract

The mechanism of the chiral VANOL-BOROX Brønsted acid catalyzed aziridination reaction of imines and ethyldiazoacetate has been studied using a combination of experimental kinetic isotope effects and theoretical calculations. A stepwise mechanism where reversible formation of a diazonium ion intermediate precedes rate-limiting ring closure to form the cis-aziridine is implicated. A revised model for the origin of enantio- and diastereoselectivity is proposed based on relative energies of the ring-closing transition structures.

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Year: 2013 PMID： 23687986 PMCID： PMC3692281 DOI： 10.1021/jo302783d

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

16 in total

1. Origins of selectivity in Brønsted acid-promoted diazoalkane-azomethine reactions (the aza-Darzens aziridine synthesis).

Authors: Timothy L Troyer; Hubert Muchalski; Ki Bum Hong; Jeffrey N Johnston
Journal: Org Lett Date: 2011-03-02 Impact factor: 6.005

2. Substrate-induced covalent assembly of a chemzyme and crystallographic characterization of a chemzyme-substrate complex.

Authors: Gang Hu; Anil K Gupta; Rui H Huang; Munmun Mukherjee; William D Wulff
Journal: J Am Chem Soc Date: 2010-10-20 Impact factor: 15.419

3. Isotope effects and heavy-atom tunneling in the Roush allylboration of aldehydes.

Authors: Mathew J Vetticatt; Daniel A Singleton
Journal: Org Lett Date: 2012-04-16 Impact factor: 6.005

Review 4. To protonate or alkylate? Stereoselective Brønsted acid catalysis of C-C bond formation using diazoalkanes.

Authors: Jeffrey N Johnston; Hubert Muchalski; Timothy L Troyer
Journal: Angew Chem Int Ed Engl Date: 2010-03-22 Impact factor: 15.336

5. How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.

Authors: Mathew J Vetticatt; Aman A Desai; William D Wulff
Journal: J Am Chem Soc Date: 2010-09-29 Impact factor: 15.419

6. Organocatalytic asymmetric direct alkylation of alpha-diazoester via C-H bond cleavage.

Authors: Daisuke Uraguchi; Keiichi Sorimachi; Masahiro Terada
Journal: J Am Chem Soc Date: 2005-07-06 Impact factor: 15.419

7. Mapping the active site in a chemzyme: diversity in the N-substituent in the catalytic asymmetric aziridination of imines.

Authors: Yu Zhang; Zhenjie Lu; Aman Desai; William D Wulff
Journal: Org Lett Date: 2008-12-04 Impact factor: 6.005

8. Trans-selective asymmetric aziridination of diazoacetamides and N-Boc imines catalyzed by axially chiral dicarboxylic acid.

Authors: Takuya Hashimoto; Nanase Uchiyama; Keiji Maruoka
Journal: J Am Chem Soc Date: 2008-10-11 Impact factor: 15.419

9. Design of axially chiral dicarboxylic acid for asymmetric Mannich reaction of arylaldehyde N-Boc imines and diazo compounds.

Authors: Takuya Hashimoto; Keiji Maruoka
Journal: J Am Chem Soc Date: 2007-07-27 Impact factor: 15.419

10. BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.

Authors: Anil K Gupta; Munmun Mukherjee; Gang Hu; William D Wulff
Journal: J Org Chem Date: 2012-09-04 Impact factor: 4.354

4 in total

1. Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Authors: Yong Guan; Zhensheng Ding; William D Wulff
Journal: Chemistry Date: 2013-10-02 Impact factor: 5.236