The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates

Ronald M Lawrence; Patrick Perlmutter

The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates

Ronald M Lawrence
, Patrick Perlmutter

School of Chemistry

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

Abstract

A new, one-pot annulation process, involving conjugate addn. of the sodium salts of di-Me (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates R CH(OH)C(CO2Me):CH2 (R = Me, Ph, 3-pyridinyl, 2-furanyl), produces a mixt. of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates I and II. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsatn. into these mols. is also described. [on SciFinder(R)]

Original language	English
Pages (from-to)	839 - 845
Number of pages	7
Journal	Australian Journal of Chemistry
Volume	49
Issue number	8
Publication status	Published - 1996

Cite this

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title = "The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates",

abstract = "A new, one-pot annulation process, involving conjugate addn. of the sodium salts of di-Me (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates R CH(OH)C(CO2Me):CH2 (R = Me, Ph, 3-pyridinyl, 2-furanyl), produces a mixt. of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates I and II. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsatn. into these mols. is also described. [on SciFinder(R)]",

author = "Lawrence, \{Ronald M\} and Patrick Perlmutter",

year = "1996",

language = "English",

volume = "49",

pages = "839 -- 845",

journal = "Australian Journal of Chemistry",

issn = "1445-0038",

publisher = "CSIRO Publishing",

number = "8",

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T1 - The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates

AU - Lawrence, Ronald M

AU - Perlmutter, Patrick

PY - 1996

Y1 - 1996

N2 - A new, one-pot annulation process, involving conjugate addn. of the sodium salts of di-Me (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates R CH(OH)C(CO2Me):CH2 (R = Me, Ph, 3-pyridinyl, 2-furanyl), produces a mixt. of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates I and II. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsatn. into these mols. is also described. [on SciFinder(R)]

AB - A new, one-pot annulation process, involving conjugate addn. of the sodium salts of di-Me (or dibenzyl) malonate to alkyl 2-(1-hydroxyalkyl)propenoates R CH(OH)C(CO2Me):CH2 (R = Me, Ph, 3-pyridinyl, 2-furanyl), produces a mixt. of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates I and II. Alkylations of the cis-isomers were found to be highly stereoselective. The introduction of unsatn. into these mols. is also described. [on SciFinder(R)]

UR - http://www.publish.csiro.au/?act=view_file&file_id=CH9960839.pdf

M3 - Article

SN - 1445-0038

VL - 49

SP - 839

EP - 845

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 8

ER -

The synthesis and some manipulations of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates

Abstract

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