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

C. Palomo; M. Oiarbide; A. K. Sharma; M. C. González-Rego; A. Linden; J. M. García; A. González

doi:10.1021/jo001031f

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

C. Palomo
, M. Oiarbide
, A. K. Sharma
, M. C. González-Rego
, A. Linden
, J. M. García
, A. González

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

(1R)-2endo-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.

Original language	English (US)
Pages (from-to)	9007-9012
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	65
Issue number	26
DOIs	https://doi.org/10.1021/jo001031f
State	Published - Dec 29 2000

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo001031f

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title = "Camphor-based α-bromo ketones for the asymmetric Darzens reaction",

abstract = "(1R)-2endo-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.",

author = "C. Palomo and M. Oiarbide and Sharma, \{A. K.\} and Gonz{\'a}lez-Rego, \{M. C.\} and A. Linden and Garc{\'i}a, \{J. M.\} and A. Gonz{\'a}lez",

year = "2000",

month = dec,

day = "29",

doi = "10.1021/jo001031f",

language = "English (US)",

volume = "65",

pages = "9007--9012",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Camphor-based α-bromo ketones for the asymmetric Darzens reaction

AU - Palomo, C.

AU - Oiarbide, M.

AU - Sharma, A. K.

AU - González-Rego, M. C.

AU - Linden, A.

AU - García, J. M.

AU - González, A.

PY - 2000/12/29

Y1 - 2000/12/29

N2 - (1R)-2endo-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.

AB - (1R)-2endo-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.

UR - https://www.scopus.com/pages/publications/0034731654

UR - https://www.scopus.com/pages/publications/0034731654#tab=citedBy

U2 - 10.1021/jo001031f

DO - 10.1021/jo001031f

M3 - Article

AN - SCOPUS:0034731654

SN - 0022-3263

VL - 65

SP - 9007

EP - 9012

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 26

ER -

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

Abstract

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