An Accidental Synthetic Chemist

David B. Collum

doi:10.1055/a-2616-1181

Synthesis, Table of Contents

Synthesis 2025; 57(21): 3158-3178
DOI: 10.1055/a-2616-1181

Short Review

Published as part of the Special Topic Dedicated to Prof. Paul Knochel

An Accidental Synthetic Chemist

Authors

David B. Collum

Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York, USA (Ringgold ID: RIN5922)

Abstract

All articles of this category

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.

Introduction
The Early Years
Lithium Amides and N-Lithiated Species
Sodium Amides
Potassium Hexamethyldisilazide and Related Potassium Alkyl(trimethylsilyl) Amides
Carbanions
Enolates
Conclusions

Keywords

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

Full Text

References

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