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Synthetic applications of ortho esters

Wipf, P and Tsuchimoto, T and Takahashi, H (1999) Synthetic applications of ortho esters. Pure and Applied Chemistry, 71 (3). 415 - 421. ISSN 0033-4545

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Abstract

The zirconocene-catalyzed rearrangement of epoxy esters to give 2,7,8-trioxabicyclo[3.2.1]octanes (ABO-esters) adds a new modification to carboxylic acid chemistry. Acid/ base-sensitive α-amino, α-hydroxy and β-bromo acid derivatives are converted in high yield to ABO-esters using this protocol. This strategy is complementary to the OBO-ester technology, and orthogonal methods for the deprotection of ABO-and OBO-esters have been developed. Using chiral epoxy alcohol derivatives, a convenient and general asymmetric synthesis of bicyclic ortho esters can be achieved. New applications of ABO-esters in organic synthesis include conjugate additions to α,β-unsaturated ortho esters and their use as homoenolate equivalents as well as the preparation of tertiary alcohols. © 1999 IUPAC.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Tsuchimoto, T
Takahashi, H
Date: 1 January 1999
Date Type: Publication
Journal or Publication Title: Pure and Applied Chemistry
Volume: 71
Number: 3
Page Range: 415 - 421
DOI or Unique Handle: 10.1351/pac199971030415
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0033-4545
Date Deposited: 06 Oct 2015 14:56
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/25624

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