Confined acids catalyze asymmetric single aldolizations of acetaldehyde enolates

Lucas Schreyer, Philip S.J. Kaib, Vijay N. Wakchaure, Carla Obradors, Roberta Properzi, Sunggi Lee, Benjamin List

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

Reactions that form a product with the same reactive functionality as that of one of the starting compounds frequently end in oligomerization. As a salient example, selective aldol coupling of the smallest, though arguably most useful, enolizable aldehyde, acetaldehyde, with just one partner substrate has proven to be extremely challenging. Here, we report a highly enantioselective Mukaiyama aldol reaction with the simple triethylsilyl (TES) and tert-butyldimethylsilyl (TBS) enolates of acetaldehyde and various aliphatic and aromatic acceptor aldehydes. The reaction is catalyzed by recently developed, strongly acidic imidodiphosphorimidates (IDPi), which, like enzymes, display a confined active site but, like small-molecule catalysts, have a broad substrate scope. The process is scalable, fast, efficient (0.5 to 1.5 mole % catalyst loading), and greatly simplifies access to highly valuable silylated acetaldehyde aldols.

Original languageEnglish
Pages (from-to)216-219
Number of pages4
JournalScience
Volume362
Issue number6411
DOIs
StatePublished - 2018

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© 2018 American Association for the Advancement of Science. All Rights Reserved.

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