Camphor-based α-bromo ketones for the asymmetric Darzens reaction

…, MC González-Rego, A Linden, JM García…

Index: Palomo; Oiarbide; Sharma; Gonzalez-Rego; Linden; Garcia; Gonzalez Journal of Organic Chemistry, 2000 , vol. 65, # 26 p. 9007 - 9012

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Citation Number: 35

Abstract

(1 R)-2-endo-Bromoacetyl-1, 7, 7-trimethylbicyclo [2.2. 1] heptan-2-ol (endo-2- bromoacetylisoborneol) 4 and its trimethylsilyl ether 3 are presented as efficient reagents for the asymmetric Darzens reaction. From the α, β-epoxy ketone adducts the chiral inductor camphor is removed, by treatment with ceric (IV) ammonium nitrate, to yield the corresponding epoxy acids which are isolated as their dicyclohexylammonium salts.

 Related Synthetic Route
N/A Structure

204577-66-2

N/A

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

N/A Structure

325483-13-4

N/A

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(+-)-threo-2,3-epoxy-valeric acid Structure

122872-27-9

(+-)-threo-2,3-...

(1R)-2-endo-bromoacetyl-2-exo-trimethylsiloxy-1,7,7-trimethylbicyclo[2.2.1]heptane Structure

325483-04-3

(1R)-2-endo-bro...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(1R)-2-endo-bromoacetyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol Structure

325483-06-5

(1R)-2-endo-bro...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(1R)-2-endo-chloroacetyl-2-exo-trimethylsiloxy-1,7,7-trimethylbicyclo[2.2.1]heptane Structure

325483-07-6

(1R)-2-endo-chl...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(2R,3S)-2-bromo-3-hydroxy-1-((1R,2R,4R)-1,7,7-trimethyl-2-((trimethylsilyl)oxy)bicyclo[2.2.1]heptan-2-yl)pentan-1-one Structure

325483-19-0

(2R,3S)-2-bromo...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(2R,3S)-2-chloro-3-hydroxy-1-((1R,2R,4R)-1,7,7-trimethyl-2-((trimethylsilyl)oxy)bicyclo[2.2.1]heptan-2-yl)pentan-1-one Structure

325483-25-8

(2R,3S)-2-chlor...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

((2S,3R)-3-phenyloxiran-2-yl)((1R,2R,4R)-1,7,7-trimethyl-2-((trimethylsilyl)oxy)bicyclo[2.2.1]heptan-2-yl)methanone Structure

325483-17-8

((2S,3R)-3-phen...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(2R,3S)-2-bromo-3-hydroxy-1-((1R,2R,4R)-1,7,7-trimethyl-2-((trimethylsilyl)oxy)bicyclo[2.2.1]heptan-2-yl)hexan-1-one Structure

325483-20-3

(2R,3S)-2-bromo...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor

(2R,3S)-2-chloro-3-hydroxy-1-((1R,2R,4R)-1,7,7-trimethyl-2-((trimethylsilyl)oxy)bicyclo[2.2.1]heptan-2-yl)hexan-1-one Structure

325483-26-9

(2R,3S)-2-chlor...

~%

(+)-Camphor Structure

464-49-3

(+)-Camphor


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