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Literature DB >> 34349297

Structure, Reactivity, and Synthetic Applications of Sodium Diisopropylamide.

Ryan A Woltornist¹, Yun Ma¹, Russell F Algera², Yuhui Zhou³, Zirong Zhang⁴, David B Collum^1,2,3,4.

Abstract

The 60-year history of sodium diisopropylamide (NaDA) is described herein. We review various preparations, solvent-dependent stabilities, and solution structures. Synthetic applications of NaDA reported to date are framed by a mechanism-driven approach, emphasizing selectivities when appropriate. We conclude with examples beyond metalation in which NaDA plays a central role and a few thoughts on where future applications could be focused.

Entities: Chemical

Keywords: mechanism; metalation; organosodium; selectivity; sodium diisopropylamide; structure

Year: 2020 PMID： 34349297 PMCID： PMC8330442 DOI： 10.1055/s-0039-1690846

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

38 in total

1. Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers.

Authors: R K Boeckman; D J Boehmler; R A Musselman
Journal: Org Lett Date: 2001-11-15 Impact factor: 6.005

2. Sodium Diisopropylamide in Tetrahydrofuran: Selectivities, Rates, and Mechanisms of Alkene Isomerizations and Diene Metalations.

Authors: Russell F Algera; Yun Ma; David B Collum
Journal: J Am Chem Soc Date: 2017-08-14 Impact factor: 15.419

3. Alkali-Metal-Mediated Synergistic Effects in Polar Main Group Organometallic Chemistry.

Authors: Stuart D Robertson; Marina Uzelac; Robert E Mulvey
Journal: Chem Rev Date: 2019-03-19 Impact factor: 60.622

4. Dynamic Kinetic Resolution of Alkenyl Cyanohydrins Derived from α,β-Unsaturated Aldehydes: Stereoselective Synthesis of E-Tetrasubstituted Olefins.

Authors: Jadab Majhi; Ben W H Turnbull; Ho Ryu; Jiyong Park; Mu-Hyun Baik; P Andrew Evans
Journal: J Am Chem Soc Date: 2019-07-22 Impact factor: 15.419

5. Sodium Diisopropylamide: Aggregation, Solvation, and Stability.

Authors: Russell F Algera; Yun Ma; David B Collum
Journal: J Am Chem Soc Date: 2017-05-30 Impact factor: 15.419

6. Antimalarials. 8. Synthesis of amino ethers as candidate antimalarials.

Authors: M P LaMontagne; M S Ao; A Markovac; J R Menke
Journal: J Med Chem Date: 1976-03 Impact factor: 7.446

7. Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines.

Authors: Yun Ma; Sean Breslin; Ivan Keresztes; Emil Lobkovsky; David B Collum
Journal: J Org Chem Date: 2008-12-19 Impact factor: 4.354

8. Catalytic asymmetric deprotonation of phosphine boranes and sulfides as a route to P-stereogenic compounds.

Authors: Jonathan J Gammon; Steven J Canipa; Peter O'Brien; Brian Kelly; Sven Taylor
Journal: Chem Commun (Camb) Date: 2008-07-17 Impact factor: 6.222

9. Flavin monooxygenase metabolism: why medicinal chemists should matter.

Authors: Gabriele Cruciani; Aurora Valeri; Laura Goracci; Roberto Maria Pellegrino; Federica Buonerba; Massimo Baroni
Journal: J Med Chem Date: 2014-07-15 Impact factor: 7.446

10. Synthetically important alkali-metal utility amides: lithium, sodium, and potassium hexamethyldisilazides, diisopropylamides, and tetramethylpiperidides.

Authors: Robert E Mulvey; Stuart D Robertson
Journal: Angew Chem Int Ed Engl Date: 2013-10-16 Impact factor: 15.336

3 in total