Design of Chiral Auxiliaries for the Allene Ether Nazarov Cyclization
- 11 April 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (17), 5328-5329
- https://doi.org/10.1021/ja069342g
Abstract
A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. α-Pyranose and β-pyranose derived auxiliaries lead to enantiomeric products.Keywords
This publication has 10 references indexed in Scilit:
- A New Approach to the Nazarov Reaction via Sequential Electrocyclic Ring Opening and Ring ClosureJournal of the American Chemical Society, 2006
- An Improved Chiral Auxiliary for the Allene Ether Version of the Nazarov CyclizationOrganic Letters, 2006
- Tandem Nazarov Cyclization−Michael Addition Sequence Catalyzed by an Ir(III) ComplexJournal of the American Chemical Society, 2006
- Stereoselective C-Glycosylation Reactions of Pyranoses: The Conformational Preference and Reactions of the Mannosyl CationThe Journal of Organic Chemistry, 2006
- Investigations into the Role of Ion Pairing in Reactions of Heteroatom-Substituted Cyclic Oxocarbenium IonsOrganic Letters, 2005
- Stereochemistry of Nucleophilic Substitution Reactions Depending upon Substituent: Evidence for Electrostatic Stabilization of Pseudoaxial Conformers of Oxocarbenium Ions by Heteroatom SubstituentsJournal of the American Chemical Society, 2003
- Cationic Cyclopentannelation of Allene EthersAccounts of Chemical Research, 2003
- Asymmetric Cyclopentannelation: Camphor-Derived AuxiliaryJournal of the American Chemical Society, 2002
- Synthesis and Absolute Stereochemistry of RoseophilinJournal of the American Chemical Society, 2001
- Asymmetric Cyclopentannelation. Chiral Auxiliary on the AlleneOrganic Letters, 2000