Enhancement of 1,2-Asymmetric Induction on CC Linkage by Use of Chiral 2-Butenylboronic Esters^†^‡

Prof. Dr. Reinhard W. Hoffmann,

Prof. Dr. Reinhard W. Hoffmann

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)

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Dipl.-Chem. Hans-Joachim Zeiss,

Corresponding Author

Dipl.-Chem. Hans-Joachim Zeiss

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)Search for more papers by this author

Prof. Dr. Reinhard W. Hoffmann,

Prof. Dr. Reinhard W. Hoffmann

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)

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Dipl.-Chem. Hans-Joachim Zeiss,

Corresponding Author

Dipl.-Chem. Hans-Joachim Zeiss

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)

Farchbereich Chemie der Universität Hans-Meerwien-Strasse, D-3550 Marburg (Germany)Search for more papers by this author

First published: March 1980

https://doi.org/10.1002/anie.198002181

Citations: 36

^†

This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

^‡

Dedicated to Professor Matthias Seefelder on the occasion of his 60th birthday

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Graphical Abstract

Combination of chiral aldehyde (1) and chiral reagent (2) (derived from 2-exo-3-exo-dihydroxy-3-endo-phenylbornane) permitted a diastereoselectivity of ca. 11:1 in the formation of alcohols (3) and (4). Cram preference and chiral control by the reagent reinforce each other.

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