ISSN:
0170-2041
Keywords:
(4S,6R)-, (4R,6S)-trans-Carveol
;
(R)-, (S)-Limonene
;
Isoprene
;
Isoprenyl ether
;
[4 + 2] Cycloaddition, diastereo-, enantioselective
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Enantioselective Terpene Syntheses by Diels-Alder Reaction of 1-(1-Arylalkoxy)-2-methyl-1,3-butadiene with IsopreneThe (R)- and (S)-1-(1-arylalkoxy)-2-methyl-1,3-butadienes 6 undergo [4 + 2] cycloadditions with excess isoprene (7) under pressure to yield not only the expected (4S,6R)- and (4R,6S)-trans-carveol (8) with up to 96% e.e. but also up to 40% of (R)- and (S)-limonene (9) with up to 93% e.e. Asymmetric induction is proposed to arise from a transition state involving definite π stacking of one molecule of isoprenyl ether and two molecules of isoprene.
Additional Material:
8 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101229
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