An Accidental Synthetic Chemist

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

Abstract

A journey is described that began as a genetics major, passed through a brief period as a formal synthetic organic chemist, and proceeded through a decades-long quest to be a physical organic–organometallic chemist. Although a preponderance of our program has emphasized elucidating fundamental principles of how aggregation and solvation influence reactivity, this review focuses on the results that have implications in organic synthesis.

1. Introduction

2. The Early Years

3. Lithium Amides and N-Lithiated Species

4. Sodium Amides

5. Potassium Hexamethyldisilazide and Related Potassium Alkyl(trimethylsilyl) Amides

6. Carbanions

7. Enolates

8. Conclusions

Keywords

aggregation - asymmetric synthesis - carbanions - enantioselectivity - lithiation - solvent effects - stereoselective synthesis - organometallic reagents

Publication History

Received: 28 February 2025

Accepted after revision: 26 March 2025

Article published online:
25 July 2025

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