Diastereoselective, Catalytic Access to Cross‐aldol Products Directly from Esters and Lactones

Adrián Moreno González, Kieran Nicholson, Natalia Llopis, Gary S. Nichol, Thomas Langer, Alejandro Baeza, Stephen Thomas*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

High oxidation-state carbonyl coupling partners including esters and lactones were reacted with enones to give aldol-type products directly using two-fold organoborane catalysis. This new retrosynthetic disconnection to aldol-type products is compatible with enolisable coupling partners, without self-condensation, and couples the high reactivity of secondary dialkylboranes with the stability of pinacolboronic esters. Excellent chemoselectivity, substrate scope (including those containing reducible functionalities and free alcohols) and diastereocontrol were achieved to access both the syn - and anti -aldol-type products. Mechanistic studies confirmed the two-fold catalytic role of the single secondary borane catalyst; boron enolate formation and formation of an aldehyde surrogate from the ester coupling parter.
Original languageEnglish
JournalAngewandte Chemie International Edition
Early online date2 Aug 2022
DOIs
Publication statusE-pub ahead of print - 2 Aug 2022

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