1327162-91-3Relevant academic research and scientific papers
Development of a Computer-Guided Workflow for Catalyst Optimization. Descriptor Validation, Subset Selection, and Training Set Analysis
Henle, Jeremy J.,Zahrt, Andrew F.,Rose, Brennan T.,Darrow, William T.,Wang, Yang,Denmark, Scott E.
supporting information, p. 11578 - 11592 (2020/07/08)
Modern, enantioselective catalyst development is driven largely by empiricism. Although this approach has fostered the introduction of most of the existing synthetic methods, it is inherently limited by the skill, creativity, and chemical intuition of the practitioner. Herein, we present a complementary approach to catalyst optimization in which statistical methods are used at each stage to streamline development. To construct the optimization informatics workflow, a number of critical components had to be subjected to rigorous validation. First, the critically important molecular descriptors were validated in two case studies to establish the importance of conformation-dependent molecular representations. Next, with a large data set available, it was possible to investigate the amount of data necessary to make predictive models with different modeling methods. Given the commercial availability of many catalyst structures, it was possible to compare models generated with algorithmically selected training sets and commercially available training sets. Finally, the augmentation of limited data sets is demonstrated in a method informed by unsupervised learning to restore the accuracy of the generated models.
Chiral phosphoric acid-catalyzed addition of thiols to N-acyl imines: Access to chiral N, S-acetals
Ingle, Gajendrasingh K.,Mormino, Michael G.,Wojtas, Lukasz,Antilla, Jon C.
supporting information; experimental part, p. 4822 - 4825 (2011/11/12)
The first catalytic asymmetric method to prepare enantioenriched N,S-acetals using chiral BINOL phosphoric acids is reported. The reaction combines N-acyl imines with thiols to generate products in excellent yield and enantioselectivity. The addition reac
