𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereoselective Synthesis of Alcohols, XLIV. Cyclization of Benzyloxy-substituted (8-Oxo-2-octenyl)boronates

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

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

No coin nor oath required. For personal study only.

✦ Synopsis

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 cyclization of the other isomers studied proceeded in a stereorandom fashion. Possible reasons for this unexpected behavior are discussed.

📜 SIMILAR VOLUMES

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

Stereoselective Synthesis of Alcohols, X
Stereoselective Synthesis of Alcohols, XLIII. Asymmetric Induction on the Intramolecular Allylboration Reaction of (8-Oxo-2-octenyl)boronates
✍ Hoffmann, Reinhard W. ;Sander, Thomas 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 757 KB

## 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.

Stereoselective synthesis of alcohols, X
Stereoselective synthesis of alcohols, XL. Stereoselective cyclization of 7-oxo-2-heptenylboronates
✍ Hoffmann, Reinhard W. ;Niel, Gilles 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 681 KB

## Abstract Intramolecular allylboration reaction of 7‐oxo‐2‐heptenyl boronates leads to 2‐vinylcyclopentanols. The cyclization proceeds in a stereospecific manner, such that the (__E__)‐allylboronate 8 is converted into __trans__‐2‐vinylcyclopentanol (2) and the (__Z__)‐allylboronate 10 into __cis