The direct introduction of carbonates α to carbonyl groups

Adrian Hall; Kerri L. Jones; Teyrnon C. Jones; Niall M. Killeen; Robert Porzig; Paul H. Taylor; Sze Chak Yau; Nicholas C. O. Tomkinson

doi:10.1055/s-2006-956473

The direct introduction of carbonates α to carbonyl groups

Adrian Hall, Kerri L. Jones, Teyrnon C. Jones, Niall M. Killeen, Robert Porzig, Paul H. Taylor, Sze Chak Yau, Nicholas C. O. Tomkinson

Pure And Applied Chemistry

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

16 Citations (Scopus)

Abstract

The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.

Original language	Undefined/Unknown
Pages (from-to)	3435-3438
Number of pages	4
Journal	Synlett
Issue number	20
DOIs	https://doi.org/10.1055/s-2006-956473
Publication status	Published - 2006

Keywords

α-oxycarbonates
carbonyl groups
hydrochloride reagents

Access to Document

10.1055/s-2006-956473

Cite this

@article{e41e9e26239e4c34a6bb89aeca9956b0,

title = "The direct introduction of carbonates α to carbonyl groups",

abstract = "The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98\% isolated yield via a proposed [3,3]-sigmatropic rearrangement. ",

keywords = " α-oxycarbonates , carbonyl groups, hydrochloride reagents ",

author = "Adrian Hall and Jones, \{Kerri L.\} and Jones, \{Teyrnon C.\} and Killeen, \{Niall M.\} and Robert Porzig and Taylor, \{Paul H.\} and Yau, \{Sze Chak\} and Tomkinson, \{Nicholas C. O.\}",

year = "2006",

doi = "10.1055/s-2006-956473",

language = "Undefined/Unknown",

pages = "3435--3438",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "20",

}

TY - JOUR

T1 - The direct introduction of carbonates α to carbonyl groups

AU - Hall, Adrian

AU - Jones, Kerri L.

AU - Jones, Teyrnon C.

AU - Killeen, Niall M.

AU - Porzig, Robert

AU - Taylor, Paul H.

AU - Yau, Sze Chak

AU - Tomkinson, Nicholas C. O.

PY - 2006

Y1 - 2006

N2 - The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.

AB - The first method for the direct formation of α-oxycarbonates from both aldehydes and ketones is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.

KW - α-oxycarbonates

KW - carbonyl groups

KW - hydrochloride reagents

U2 - 10.1055/s-2006-956473

DO - 10.1055/s-2006-956473

M3 - Article

SN - 0936-5214

SP - 3435

EP - 3438

JO - Synlett

JF - Synlett

IS - 20

ER -