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DOI: 10.1055/s-0042-1751420
Carbonyl Allylation and Crotylation: Historical Perspective, Relevance to Polyketide Synthesis, and Evolution of Enantioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer Processes
The Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1-GM069445) are acknowledged for partial support of this research.
Abstract
The evolution of methods for carbonyl allylation and crotylation of alcohol proelectrophiles culminating in the design of iodide-bound ruthenium-JOSIPHOS catalysts is prefaced by a brief historical perspective on asymmetric carbonyl allylation and its relevance to polyketide construction. Using gaseous allene or butadiene as precursors to allyl- or crotylruthenium nucleophiles, respectively, new capabilities for carbonyl allylation and crotylation have been unlocked, including stereo- and site-selective methods for the allylation and crotylation of 1,3-diols and related polyols.
1 Introduction and Historical Perspective
2 Ruthenium-Catalyzed Conversion of Lower Alcohols into Higher Alcohols
3 Conclusion and Future Outlook
Publication History
Received: 16 December 2022
Accepted after revision: 16 January 2023
Article published online:
20 February 2023
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For selected examples of chiral reagents for asymmetric carbonyl allylmetalation, see:
For selected reviews on catalytic enantioselective carbonyl allylation and crotylation, see:
For selected reviews on polyketide total synthesis, see:
For selected reviews on polyketide natural products in pharmaceutical and agrochemical research, see:
With the exception of eribulin, all polyketides used in human medicine derive from soil bacteria, yet <5% of soil bacteria are amenable to culture with many phyla having eluded culture and the few bacteria amenable to culture express <10% of their biosynthetic genes:
Lower estimates of microbial diversity appear to undercount bacterial species associated with higher organisms:
Although saturated, stereochemically rich small molecules (like polyketides) have a higher success rate than related sp2-rich small-molecule clinical candidates, new synthetic methods to prepare compounds of this type are underutilized by medicinal chemists:
For selected reviews on enantioselective carbonyl addition, see:
For selected reviews on metal-catalyzed carbonyl reductive coupling, see:
For selected reviews on hydrogen auto-transfer for the conversion of lower alcohols to higher alcohols, see:
For selected reviews on ‘borrowing hydrogen’ for hydroxyl substitution, see:
For enantioselective iridium-catalyzed carbonyl allylation and crotylation, see:
For stoichiometric reactions of HXRu(CO)(PR3)3 (X = Cl, Br) with allenes or dienes to form discrete π-allylruthenium complexes, see:
Related crotylmagnesium and crotylzinc reagents bearing 2-trimethylsilyl groups react with aldehydes to give the syn-diastereomers:
For selected studies of formyl CH hydrogen bonding, see:
For selected reviews on halide counterion effects in metal catalysis, see:
Production data are taken from:
or
For selected reviews on enantioselective catalysis via chiral-at-metal complexes, see:
For other enantioselective ruthenium-catalyzed carbonyl additions via hydrogen auto-transfer that are relevant to polyketide construction, see: