1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes

Norazah Bazar; Sam Donnelly; Hao Liu; Eric J. Thomas

doi:10.1055/s-0029-1219357

1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes

Norazah Bazar
, Sam Donnelly
, Hao Liu
, Eric J. Thomas

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

Abstract

The reaction of 5-benzyloxy-2,4-dimethylpent-2-enyl bromide with the bismuth species generated by reduction of bismuth(III) iodide by zinc powder gives an intermediate which reacts with aldehydes with useful levels of stereocontrol in favour of 1,5-anti-(3E)-5-methylalk-3-enols. Manipulation of protecting groups, stereoselective hydrogenation, and tosylate displacement using a higher-order cyanomethylcuprate leads to either all-syn or anti, anti-1,3,5-disposed trimethylalkanes. © Georg Thieme Verlag Stuttgart.

Original language	English
Article number	D34809ST
Pages (from-to)	575-578
Number of pages	3
Journal	SYNLETT
Issue number	4
DOIs	https://doi.org/10.1055/s-0029-1219357
Publication status	Published - 2010

Keywords

Aldehydes
Allylation
Diastereoselectivity
Hydrogenation
Organometallic reagents

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10.1055/s-0029-1219357

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title = "1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes",

abstract = "The reaction of 5-benzyloxy-2,4-dimethylpent-2-enyl bromide with the bismuth species generated by reduction of bismuth(III) iodide by zinc powder gives an intermediate which reacts with aldehydes with useful levels of stereocontrol in favour of 1,5-anti-(3E)-5-methylalk-3-enols. Manipulation of protecting groups, stereoselective hydrogenation, and tosylate displacement using a higher-order cyanomethylcuprate leads to either all-syn or anti, anti-1,3,5-disposed trimethylalkanes. {\textcopyright} Georg Thieme Verlag Stuttgart.",

keywords = "Aldehydes, Allylation, Diastereoselectivity, Hydrogenation, Organometallic reagents",

author = "Norazah Bazar and Sam Donnelly and Hao Liu and Thomas, \{Eric J.\}",

year = "2010",

doi = "10.1055/s-0029-1219357",

language = "English",

pages = "575--578",

journal = "SYNLETT",

issn = "1437-2096",

publisher = "Georg Thieme Verlag",

number = "4",

}

TY - JOUR

T1 - 1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes

AU - Bazar, Norazah

AU - Donnelly, Sam

AU - Liu, Hao

AU - Thomas, Eric J.

PY - 2010

Y1 - 2010

N2 - The reaction of 5-benzyloxy-2,4-dimethylpent-2-enyl bromide with the bismuth species generated by reduction of bismuth(III) iodide by zinc powder gives an intermediate which reacts with aldehydes with useful levels of stereocontrol in favour of 1,5-anti-(3E)-5-methylalk-3-enols. Manipulation of protecting groups, stereoselective hydrogenation, and tosylate displacement using a higher-order cyanomethylcuprate leads to either all-syn or anti, anti-1,3,5-disposed trimethylalkanes. © Georg Thieme Verlag Stuttgart.

AB - The reaction of 5-benzyloxy-2,4-dimethylpent-2-enyl bromide with the bismuth species generated by reduction of bismuth(III) iodide by zinc powder gives an intermediate which reacts with aldehydes with useful levels of stereocontrol in favour of 1,5-anti-(3E)-5-methylalk-3-enols. Manipulation of protecting groups, stereoselective hydrogenation, and tosylate displacement using a higher-order cyanomethylcuprate leads to either all-syn or anti, anti-1,3,5-disposed trimethylalkanes. © Georg Thieme Verlag Stuttgart.

KW - Aldehydes

KW - Allylation

KW - Diastereoselectivity

KW - Hydrogenation

KW - Organometallic reagents

U2 - 10.1055/s-0029-1219357

DO - 10.1055/s-0029-1219357

M3 - Article

SN - 1437-2096

SP - 575

EP - 578

JO - SYNLETT

JF - SYNLETT

IS - 4

M1 - D34809ST

ER -

1,5-stereocontrol in bismuth-mediated reactions between aldehydes and allyl bromides: Stereoselective synthesis of open-chain all-syn- and anti, anti-1,3,5-disposed trimethylalkanes

Abstract

Keywords

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