One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions

Adeem Mahmood; Jose Ramon Suarez; Stephen P. Thomas; Varinder K. Aggarwal

doi:10.1016/j.tetlet.2012.10.091

One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions

Adeem Mahmood, Jose Ramon Suarez, Stephen P. Thomas, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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Abstract

2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	49-51
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	1
Early online date	26 Oct 2012
DOIs	https://doi.org/10.1016/j.tetlet.2012.10.091
Publication status	Published - 2 Jan 2013

Keywords

Lithiation-borylation
Allylation
Prins cyclisation
Tandem
Boronic ester
STEREOCONTROLLED SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
BORONIC ESTERS
ETHERS
ALDEHYDES
ALCOHOLS
BORANES
HYDROBORATION
DIHYDROPYRANS
REARRANGEMENT

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10.1016/j.tetlet.2012.10.091

AggarwalTHPMnuscript
NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters . Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters 54 (2013) 49–5, DOI 10.1016/j.tetlet.2012.10.091
Accepted author manuscript, 436 KB

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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research
GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/07 → 1/04/13
Project: Research

Cite this

@article{c92c3d01829e45638d0fe7e047a69025,

title = "One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions",

abstract = "2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.",

keywords = "Lithiation-borylation, Allylation, Prins cyclisation, Tandem, Boronic ester, STEREOCONTROLLED SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, BORONIC ESTERS, ETHERS, ALDEHYDES, ALCOHOLS, BORANES, HYDROBORATION, DIHYDROPYRANS, REARRANGEMENT",

author = "Adeem Mahmood and Suarez, {Jose Ramon} and Thomas, {Stephen P.} and Aggarwal, {Varinder K.}",

year = "2013",

month = jan,

day = "2",

doi = "10.1016/j.tetlet.2012.10.091",

language = "English",

volume = "54",

pages = "49--51",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "1",

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TY - JOUR

T1 - One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions

AU - Mahmood, Adeem

AU - Suarez, Jose Ramon

AU - Thomas, Stephen P.

AU - Aggarwal, Varinder K.

PY - 2013/1/2

Y1 - 2013/1/2

N2 - 2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

AB - 2,3,4,5,6-Pentasubstituted tetrahydropyrans have been prepared in good yield (42-57%) with excellent dr (>95:5) and er (>95:5) using a one-pot lithiation-borylation, allylation and Prins cyclisation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

KW - Lithiation-borylation

KW - Allylation

KW - Prins cyclisation

KW - Tandem

KW - Boronic ester

KW - STEREOCONTROLLED SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - BORONIC ESTERS

KW - ETHERS

KW - ALDEHYDES

KW - ALCOHOLS

KW - BORANES

KW - HYDROBORATION

KW - DIHYDROPYRANS

KW - REARRANGEMENT

U2 - 10.1016/j.tetlet.2012.10.091

DO - 10.1016/j.tetlet.2012.10.091

M3 - Article (Academic Journal)

SN - 0040-4039

VL - 54

SP - 49

EP - 51

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 1

ER -

One-pot synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans using lithiation-borylation, allylation and Prins cyclisation reactions

Abstract

Keywords

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Projects

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

GENERAL AND CONVERGENT STRATEGY FOR ASYMMETRIC SYNTHESIS

Cite this