Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 1994; 1994(12): 1313-1321
DOI: 10.1055/s-1994-25687
DOI: 10.1055/s-1994-25687
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Synthesis of Highly Functionalized, Enantiomerically and Diastereomerically Pure Cyclohexane Derivates via Michael Addition of Chiral 3-Tosyl-2-(2-oxoalkyl)-1,3-oxazolidines and Methyl Vinyl Ketone
Further Information
Publication History
Publication Date:
25 April 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/199412/lookinside/thumbnails/10.1055-s-1994-25687-1.jpg)
2-(2-Oxocycloalkyl)- or 2-phenylacyl-3-tosyl-1,3-oxazolidines 1, 2, 9, and 10 undergo with 3-buten-2-one highly diastereoselective Michael additions under the influence of cesium carbonate to yield 1,5-diketones 8 or 11, respectively. Intramolecular aldolization of diketones 8 yields stereohomogeneous cyclohexanones 13 or 14. Addition of nucleophiles to ketones 14, again, proceeds highly stereoselectively to give diols 17. Overall, under the stereodirecting influence of N-tosyl-2-aminoalkanols, stereohomogeneous protected carbaldehydes are constructed within a few steps from simple achiral precursors.