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Synthesis 2017; 49(03): 484-503
DOI: 10.1055/s-0036-1588888
DOI: 10.1055/s-0036-1588888
short review
Substrate-Controlled Aldol Reactions from Chiral α-Hydroxy Ketones
Further Information
Publication History
Received: 26 July 2016
Accepted after revision: 02 September 2016
Publication Date:
12 October 2016 (online)
Dedicated to Professor Clayton H. Heathcock on the occasion of his 80th birthday
Abstract
Chiral α-hydroxy ketones are valuable platforms from which highly stereoselective substrate-controlled aldol reactions may be performed. The suitable choice of the hydroxyl protecting group and the enolization conditions produce aldol adducts that can be easily manipulated to give a variety of enantiomerically pure compounds. Moreover, such aldol reactions often play a crucial role in the coupling of elaborate fragments in advanced steps of the synthesis of natural products. Together, these features confer to the α-hydroxy ketones a prominent position among the chiral substrates that are capable of providing highly asymmetric transformations.
1 Introduction
2 Pioneering Contributions
3 Boron-Mediated Aldol Reactions from α-Hydroxy Ethyl Ketones
4 Titanium-Mediated Aldol Reactions from α-Hydroxy Ethyl Ketones
5 Other Aldol Reactions from α-Hydroxy Ethyl Ketones
6 Aldol Reactions from α-Hydroxy Methyl Ketones
7 Conclusions
-
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For theoretical studies on the aldol reaction from Z-borinates, see:
For theoretical studies on the enolization of ketones by L2BCl, see:
For theoretical studies on the aldol reaction from E-borinates, see:
For key interactions with the aldehyde proton, see:
For other examples, see:
For other examples, see:
For some reviews on the impact of Mukaiyama aldol reaction in the synthesis of natural products, see:
For other lithium-mediated aldol reactions from α,β-dihydroxy methyl ketones for the synthesis of amphidinolides, see: