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A Convenient Stereoselective Synthesis of (1 R ,2 S ,3 R ,4 S )‐3‐(Neopentyloxy)isoborneol
Author(s) -
Verdaguer Xavier,
Marchueta Iolanda,
Tormo Jordi,
Moyano Albert,
Pericàs Miquel A.,
Riera Antoni
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810109
Subject(s) - chemistry , yield (engineering) , moiety , stereoselectivity , hydrolysis , acetal , chiral auxiliary , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , physics , thermodynamics
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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