Journal article
Cp2ZrMeCl: A reagent for asymmetric methyl addition.
- Abstract:
- The use of Cp2ZrMeCl is described as a source of nucleophilic methyl in asymmetric catalysis. This easily prepared reagent is bench stable, weighable in air, and generally useful in highly enantioselective copper-catalyzed addition reactions at room temperature. Methyl is successfully (generally > 90% ee) added in 1,4-additions to cyclic and acyclic α,β-unsaturated ketones, to provide tertiary and quaternary centers. Examples of catalyst controlled diastereoselective 1,6-addition and dynamic kinetic asymmetric allylic alkylation reactions are also reported. The reagent is used in the catalytic asymmetric synthesis of naturally occurring fragrance (R)-(−)-muscone (82% yield, 91% ee).
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 450.8KB, Terms of use)
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- Publisher copy:
- 10.1021/acs.orglett.6b01829
Authors
+ Engineering and Physical Sciences Research Council
More from this funder
- Grant:
- CentreforDoctoralTraininginSynthesisforBiology
- Medi-cine(EP/L015838/1)
- EP/M002144/1
- EP/M025241/1
- EP/N022246/1
- Publisher:
- American Chemical Society
- Journal:
- Organic Letters More from this journal
- Volume:
- 18
- Issue:
- 15
- Pages:
- 3814–3817
- Publication date:
- 2016-07-26
- Acceptance date:
- 2016-07-18
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- Pubs id:
-
pubs:635394
- UUID:
-
uuid:0b7156d3-a554-4be6-b168-84ebfc47d942
- Local pid:
-
pubs:635394
- Source identifiers:
-
635394
- Deposit date:
-
2016-07-26
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2016
- Notes:
- © American Chemical Society 2016. This is the accepted manuscript version of the article. The final version is available online from ACS at: [10.1021/acs.orglett.6b01829]
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