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Synthesis 2013; 45(16): 2222-2233
DOI: 10.1055/s-0033-1339285
DOI: 10.1055/s-0033-1339285
feature article
Boron–Zinc Exchange in The Diastereoselective Arylation of Sugar-Based Aldehydes: Stereoselective Synthesis of (+)-7-epi-Goniofufurone and Analogues
Weitere Informationen
Publikationsverlauf
Received: 12. April 2013
Accepted after revision: 15. Mai 2013
Publikationsdatum:
10. Juli 2013 (online)
Abstract
The substrate-controlled diastereoselective arylation of chiral aldehydes readily available from carbohydrates is described, using the boron–zinc exchange reaction to generate the transferable aryl groups. The methodology developed was applied to the total synthesis of the styryllactone (+)-7-epi-goniofufurone and analogues thereof.
Key words
arylzinc reagents - boron–zinc exchange - diastereoselective addition - chelation control - styryllactonesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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For the addition of aryl Grignard reagents:
For the addition of arylaluminum reagents:
For the addition of aryltitanium reagents:
For earlier reports on the B–Zn exchange, see:
For selected recent references on the asymmetric addition of arylzincs to aldehydes, see:
For theoretical studies on the mechanism of the arylation of aldehydes:
Aldehyde 1
Aldehyde 2:
Aldehyde 3: