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New Chiral Building Blocks and Branched 1,6‐Anhydro Sugars from Regio‐ and Stereoisomeric Černý Epoxides
Author(s) -
Krohn Karsten,
Gehle Dietmar,
Flörke Ulrich
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500242
Subject(s) - chemistry , epoxide , yield (engineering) , alcohol , organic chemistry , allyl alcohol , stereochemistry , catalysis , materials science , metallurgy
The tandem epoxide→allyl alcohol rearrangement–cuprate cross‐coupling previously described for the Černý epoxide 1 , to yield the allyl alcohol 2 , was extended to the regioisomeric epoxy‐tosylate 3, to yield allyl alcohol 4 , and to the stereoisomeric epoxide 5 to afford the allyl alcohols of type 6 . Further transformation of the products from this new two‐step one‐pot reaction afforded regio‐ and stereodiverse branched 1,6‐anhydrosugars of potential use as building blocks in natural product synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)