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Stereoselective Synthesis of Alcohols, XLII. Stereoselective Cyclization of (8-Oxo-2-octenyl)boronates tocis- ortrans-2-Vinylcyclohexanol

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

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

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✦ Synopsis

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 diastereoselectivity exceeding 99.8%.

📜 SIMILAR VOLUMES

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

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## 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
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## 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