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A Convenient Stereoselective Synthesis of (1R,2S,3R,4S)-3-(Neopentyloxy)isoborneol

✍ Scribed by Xavier Verdaguer; Iolanda Marchueta; Jordi Tormo; Albert Moyano; Miquel A. Pericàs; Antoni Riera

Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
465 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A convenient preparation of (1__R__,2__S__,3__R__,4__S__)‐3‐(neopentyloxy)isoborneol (= (1__R__,2__S__,3__R__,4__S__)‐3‐(2,2‐dimethyl‐propoxy)‐1,7,7‐trimethylbicyclo[2.2.1]heptan‐2‐ol; 1a), a valuable chiral auxiliary, is described. The synthesis involves six steps starting from the readily available camphorquinone (5) and gives 1a in 48% overall yield. The key step is the chemoselective hydrolysis of the less hindered 1,3‐dioxolane moiety in the camphorquinone di‐acetal 4.

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ChemInform Abstract: A Convenient Stereo
ChemInform Abstract: A Convenient Stereoselective Synthesis of (1R,2S,3R,4S)-3-(Neopentyloxy)isoborneol.
✍ X. VERDAGUER; I. MARCHUETA; J. TORMO; A. MOYANO; M. A. PERICAS; A. RIERA 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 1 views

A Convenient Stereoselective Synthesis of (1R,2S,3R,4S)-3-(Neopentyloxy)isoborneol. -The first regio-and stereoselective synthesis of the title compound (VI), a valuable chiral auxiliary, is developed starting from the camphorquinone (I) in six steps and 48% overall yield. -