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Stereoselective Synthesis of Alcohols, XLIII. Asymmetric Induction on the Intramolecular Allylboration Reaction of (8-Oxo-2-octenyl)boronates

✍ Scribed by Hoffmann, Reinhard W. ;Sander, Thomas

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
757 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The cyclization of (8‐oxo‐2‐octenyl)boronates having methyl substituents in the chain linking the two functional groups proceeds with complete simple diastereoselectivity and with induced diastereoselectivity of 85 to > 98% to give methylsubstituted 2‐vinylcyclohexanols.

📜 SIMILAR VOLUMES

Stereoselective Synthesis of Alcohols, X
Stereoselective Synthesis of Alcohols, XLIV. Cyclization of Benzyloxy-substituted (8-Oxo-2-octenyl)boronates
✍ Sander, Thomas ;Hoffmann, Reinhard W. 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 866 KB

## Abstract The cyclization of (8‐oxo‐2‐octenyl)boronates having benzyloxy substituents in the chain linking the two functional groups gives benzyloxy‐substituted 2‐vinylcyclohexanols. High asymmetric induction is found for the 4‐ or 6‐benzyloxy‐(__Z__)‐octenylboronates 12a and 12c, whereas cycliza

Stereoselective Synthesis of Alcohols, X
Stereoselective Synthesis of Alcohols, XLII. Stereoselective Cyclization of (8-Oxo-2-octenyl)boronates tocis- ortrans-2-Vinylcyclohexanol
✍ Hoffmann, Reinhard W. ;Sander, Thomas ;Hense, Achim 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 553 KB

## Abstract Intramolecular allylboration reactions of (8‐oxo‐2‐octenyl)boronates proceed with excellent diastereoselectivity: the __E__‐isomer 1d leads to the __trans__‐2‐vinylcyclohexanol (2) with 99.5% d.s., the corresponding Z‐isomer 3d cyclizes to give the __cis__‐isomer with a diastereoselecti