1,5-Stereocontrol in reactions of 5-benzyloxy-4-methylpent-2-enyl bromides with aldehydes mediated by Bi(0): Synthesis of aliphatic compounds with 1,5-syn-related methyl groups

Sam Donnelly; Eric J. Thomas; Mark Fielding; Angela Thomas

doi:10.1016/j.tetlet.2004.07.035

1,5-Stereocontrol in reactions of 5-benzyloxy-4-methylpent-2-enyl bromides with aldehydes mediated by Bi(0): Synthesis of aliphatic compounds with 1,5-syn-related methyl groups

Sam Donnelly, Eric J. Thomas, Mark Fielding, Angela Thomas

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

Abstract

Treatment of the 5-benzyloxy-4-methylpent-2-enyl bromide 6 with the low valent bismuth species formed by reduction of bismuth(III) iodide with zinc powder generates an intermediate, which reacts with aldehydes with useful levels of 1,5-stereocontrol in favour of the 1,5-anti-(E)-isomers 4. These products were used to prepared aliphatic compounds with 1,5-syn-related methyl groups. © 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	6779-6782
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	36
DOIs	https://doi.org/10.1016/j.tetlet.2004.07.035
Publication status	Published - 30 Aug 2004

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title = "1,5-Stereocontrol in reactions of 5-benzyloxy-4-methylpent-2-enyl bromides with aldehydes mediated by Bi(0): Synthesis of aliphatic compounds with 1,5-syn-related methyl groups",

abstract = "Treatment of the 5-benzyloxy-4-methylpent-2-enyl bromide 6 with the low valent bismuth species formed by reduction of bismuth(III) iodide with zinc powder generates an intermediate, which reacts with aldehydes with useful levels of 1,5-stereocontrol in favour of the 1,5-anti-(E)-isomers 4. These products were used to prepared aliphatic compounds with 1,5-syn-related methyl groups. {\textcopyright} 2004 Elsevier Ltd. All rights reserved.",

author = "Sam Donnelly and Thomas, {Eric J.} and Mark Fielding and Angela Thomas",

year = "2004",

month = aug,

day = "30",

doi = "10.1016/j.tetlet.2004.07.035",

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journal = "Tetrahedron Letters",

issn = "1873-3581",

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T1 - 1,5-Stereocontrol in reactions of 5-benzyloxy-4-methylpent-2-enyl bromides with aldehydes mediated by Bi(0): Synthesis of aliphatic compounds with 1,5-syn-related methyl groups

AU - Donnelly, Sam

AU - Thomas, Eric J.

AU - Fielding, Mark

AU - Thomas, Angela

PY - 2004/8/30

Y1 - 2004/8/30

N2 - Treatment of the 5-benzyloxy-4-methylpent-2-enyl bromide 6 with the low valent bismuth species formed by reduction of bismuth(III) iodide with zinc powder generates an intermediate, which reacts with aldehydes with useful levels of 1,5-stereocontrol in favour of the 1,5-anti-(E)-isomers 4. These products were used to prepared aliphatic compounds with 1,5-syn-related methyl groups. © 2004 Elsevier Ltd. All rights reserved.

AB - Treatment of the 5-benzyloxy-4-methylpent-2-enyl bromide 6 with the low valent bismuth species formed by reduction of bismuth(III) iodide with zinc powder generates an intermediate, which reacts with aldehydes with useful levels of 1,5-stereocontrol in favour of the 1,5-anti-(E)-isomers 4. These products were used to prepared aliphatic compounds with 1,5-syn-related methyl groups. © 2004 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2004.07.035

DO - 10.1016/j.tetlet.2004.07.035

M3 - Article

SN - 1873-3581

VL - 45

SP - 6779

EP - 6782

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

1,5-Stereocontrol in reactions of 5-benzyloxy-4-methylpent-2-enyl bromides with aldehydes mediated by Bi(0): Synthesis of aliphatic compounds with 1,5-syn-related methyl groups

Abstract

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