Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles

Oliver R. S. John; Niall M. Killeen; Deborah A. Knowles; Sze Chak Yau; Mark C. Bagley; Nicholas C. O. Tomkinson

doi:10.1021/ol701774y

Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles

Oliver R. S. John, Niall M. Killeen, Deborah A. Knowles, Sze Chak Yau, Mark C. Bagley, Nicholas C. O. Tomkinson

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

35 Citations (Scopus)

Abstract

N-Methyl-O-tosylhydroxylamine (I) is an effective reagent for the direct α-oxytosylation of carbonyl compds. The reactions proceed smoothly at room temp. in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsym. substrates, regioselectivity for primary over secondary centers is obsd. and complete regiospecificity for primary over tertiary centers is obtained. E.g., reaction of I and PhCOCH2CH3 gave 48% PhCOCHMeOTs. Addn. of a bis-heteronucleophile directly to the crude reaction mixt. in a one-pot process leads to the corresponding heterocyclic product. E.g., reaction of I and acetone, followed by addn. of H2NCSPh, gave 69% 4-methyl-2-phenylthiazole. [on SciFinder(R)]

Original language	English
Pages (from-to)	4009-4012
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	20
DOIs	https://doi.org/10.1021/ol701774y
Publication status	Published - 2007

Keywords

carbonyl compounds
one-pot synthesis
heterocycles

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10.1021/ol701774y

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@article{33da25b02c8a4ef7a8d2dd4837b55101,

title = "Direct α-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles",

abstract = "N-Methyl-O-tosylhydroxylamine (I) is an effective reagent for the direct α-oxytosylation of carbonyl compds. The reactions proceed smoothly at room temp. in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsym. substrates, regioselectivity for primary over secondary centers is obsd. and complete regiospecificity for primary over tertiary centers is obtained. E.g., reaction of I and PhCOCH2CH3 gave 48% PhCOCHMeOTs. Addn. of a bis-heteronucleophile directly to the crude reaction mixt. in a one-pot process leads to the corresponding heterocyclic product. E.g., reaction of I and acetone, followed by addn. of H2NCSPh, gave 69% 4-methyl-2-phenylthiazole. [on SciFinder(R)]",

keywords = "carbonyl compounds , one-pot synthesis , heterocycles",

author = "John, {Oliver R. S.} and Killeen, {Niall M.} and Knowles, {Deborah A.} and Yau, {Sze Chak} and Bagley, {Mark C.} and Tomkinson, {Nicholas C. O.}",

year = "2007",

doi = "10.1021/ol701774y",

language = "English",

volume = "9",

pages = "4009--4012",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

TY - JOUR

T1 - Direct α-oxytosylation of carbonyl compounds

T2 - one-pot synthesis of heterocycles

AU - John, Oliver R. S.

AU - Killeen, Niall M.

AU - Knowles, Deborah A.

AU - Yau, Sze Chak

AU - Bagley, Mark C.

AU - Tomkinson, Nicholas C. O.

PY - 2007

Y1 - 2007

N2 - N-Methyl-O-tosylhydroxylamine (I) is an effective reagent for the direct α-oxytosylation of carbonyl compds. The reactions proceed smoothly at room temp. in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsym. substrates, regioselectivity for primary over secondary centers is obsd. and complete regiospecificity for primary over tertiary centers is obtained. E.g., reaction of I and PhCOCH2CH3 gave 48% PhCOCHMeOTs. Addn. of a bis-heteronucleophile directly to the crude reaction mixt. in a one-pot process leads to the corresponding heterocyclic product. E.g., reaction of I and acetone, followed by addn. of H2NCSPh, gave 69% 4-methyl-2-phenylthiazole. [on SciFinder(R)]

AB - N-Methyl-O-tosylhydroxylamine (I) is an effective reagent for the direct α-oxytosylation of carbonyl compds. The reactions proceed smoothly at room temp. in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsym. substrates, regioselectivity for primary over secondary centers is obsd. and complete regiospecificity for primary over tertiary centers is obtained. E.g., reaction of I and PhCOCH2CH3 gave 48% PhCOCHMeOTs. Addn. of a bis-heteronucleophile directly to the crude reaction mixt. in a one-pot process leads to the corresponding heterocyclic product. E.g., reaction of I and acetone, followed by addn. of H2NCSPh, gave 69% 4-methyl-2-phenylthiazole. [on SciFinder(R)]

KW - carbonyl compounds

KW - one-pot synthesis

KW - heterocycles

U2 - 10.1021/ol701774y

DO - 10.1021/ol701774y

M3 - Article

VL - 9

SP - 4009

EP - 4012

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -