Alkene anti-dihydroxylation with malonoyl peroxides

Carla Alamillo-Ferrer; Stuart C. Davidson; Michael J. Rawling; Natalie H. Theodoulou; Matthew Campbell; Philip G. Humphreys; Alan R. Kennedy; Nicholas C. O. Tomkinson

doi:10.1021/acs.orglett.5b02674

Alkene anti-dihydroxylation with malonoyl peroxides

Carla Alamillo-Ferrer, Stuart C. Davidson, Michael J. Rawling, Natalie H. Theodoulou, Matthew Campbell, Philip G. Humphreys, Alan R. Kennedy, Nicholas C. O. Tomkinson^*

^*Corresponding author for this work

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

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Abstract

Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

Original language	English
Pages (from-to)	5132-5135
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.5b02674
Publication status	Published - 16 Oct 2015

Keywords

anti-Dihydroxylation
Malonoyl Peroxides
alkenes
alkaline hydrolysis

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10.1021/acs.orglett.5b02674

Ferrer-etal-OL-2015-Alkene-anti-dihydroxylation-with-malonoylAccepted author manuscript, 1.74 MB

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title = "Alkene anti-dihydroxylation with malonoyl peroxides",

abstract = "Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.",

keywords = "anti-Dihydroxylation, Malonoyl Peroxides, alkenes, alkaline hydrolysis",

author = "Carla Alamillo-Ferrer and Davidson, {Stuart C.} and Rawling, {Michael J.} and Theodoulou, {Natalie H.} and Matthew Campbell and Humphreys, {Philip G.} and Kennedy, {Alan R.} and Tomkinson, {Nicholas C. O.}",

year = "2015",

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day = "16",

doi = "10.1021/acs.orglett.5b02674",

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journal = "Organic Letters",

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TY - JOUR

T1 - Alkene anti-dihydroxylation with malonoyl peroxides

AU - Alamillo-Ferrer, Carla

AU - Davidson, Stuart C.

AU - Rawling, Michael J.

AU - Theodoulou, Natalie H.

AU - Campbell, Matthew

AU - Humphreys, Philip G.

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C. O.

PY - 2015/10/16

Y1 - 2015/10/16

N2 - Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

AB - Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

KW - anti-Dihydroxylation

KW - Malonoyl Peroxides

KW - alkenes

KW - alkaline hydrolysis

UR - http://www.scopus.com/inward/record.url?scp=84944929930&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b02674

DO - 10.1021/acs.orglett.5b02674

M3 - Article

AN - SCOPUS:84944929930

SN - 1523-7060

VL - 17

SP - 5132

EP - 5135

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Alkene anti-dihydroxylation with malonoyl peroxides

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Alkene anti-dihydroxylation with malonoyl peroxides

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