Work

Design of Organocatalysts for Asymmetric Propargylations through Computational Screening

Year: 2016

Type: article

Abstract: The development of asymmetric catalysts is typically driven by the experimental screening of potential catalyst designs. Herein, we demonstrate the design of asymmetric propargylation catalysts through computational screening. This was done using our computational toolkit AARON (automated alkylation reaction optimizer for N-oxides), which automates the prediction of enantioselectivities for bidentate Lewis base catalyzed alkylation reactions. A systematic screening of 59 potential catalysts built on 6 bipyridine N,N′-dioxide-derived scaffolds results in predicted ee values for the propargylation of benzaldehyde ranging from 45% (S) to 99% (R), with 12 ee values exceeding 95%. These data provide a broad set of experimentally testable predictions. Moreover, the associated data revealed key details regarding the role of stabilizing electrostatic interactions in asymmetric propargylations, which were harnessed in the design of a propargylation catalyst for which the predicted ee exceeds 99%.

Source: ACS Catalysis

DOI: 10.1021/acscatal.6b02366

Authors: Analise C. Doney, Benjamin J. Rooks, Tongxiang Lu, Steven E. Wheeler

Institution: Texas A&M University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Welch Foundation, Texas A and M University, High Performance Research Computing, Texas A and M University, Division of Chemistry