Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

Emeline Vedrenne; Olov A. Wallner; Maxime Vitale; Frank Schmidt; Varinder K. Aggarwal

doi:10.1021/ol802651b

Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

Emeline Vedrenne, Olov A. Wallner, Maxime Vitale, Frank Schmidt, Varinder K. Aggarwal^*

^*Corresponding author for this work

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

61 Citations (Scopus)

Abstract

Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

Original language	English
Pages (from-to)	165-168
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	1
DOIs	https://doi.org/10.1021/ol802651b
Publication status	Published - 1 Jan 2009

Keywords

STEREOSELECTIVE-SYNTHESIS
ASYMMETRIC DIHYDROXYLATION
TETRASUBSTITUTED OXIRANES
TERMINAL EPOXIDES
CHIRAL CARBENOIDS
WITTIG REACTION
CHEMISTRY
BORANES
ALKENES
ORGANOBORANES

Access to Document

10.1021/ol802651b

Handle.net

Persistent link

Cite this

@article{b6eba1884795478d8e4ed1dc34af4099,

title = "Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols",

abstract = "Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.",

keywords = "STEREOSELECTIVE-SYNTHESIS, ASYMMETRIC DIHYDROXYLATION, TETRASUBSTITUTED OXIRANES, TERMINAL EPOXIDES, CHIRAL CARBENOIDS, WITTIG REACTION, CHEMISTRY, BORANES, ALKENES, ORGANOBORANES",

author = "Emeline Vedrenne and Wallner, {Olov A.} and Maxime Vitale and Frank Schmidt and Aggarwal, {Varinder K.}",

year = "2009",

month = jan,

day = "1",

doi = "10.1021/ol802651b",

language = "English",

volume = "11",

pages = "165--168",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "1",

}

TY - JOUR

T1 - Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

AU - Vedrenne, Emeline

AU - Wallner, Olov A.

AU - Vitale, Maxime

AU - Schmidt, Frank

AU - Aggarwal, Varinder K.

PY - 2009/1/1

Y1 - 2009/1/1

N2 - Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

AB - Lithiated epoxides react stereospecifically with boronic esters to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.

KW - STEREOSELECTIVE-SYNTHESIS

KW - ASYMMETRIC DIHYDROXYLATION

KW - TETRASUBSTITUTED OXIRANES

KW - TERMINAL EPOXIDES

KW - CHIRAL CARBENOIDS

KW - WITTIG REACTION

KW - CHEMISTRY

KW - BORANES

KW - ALKENES

KW - ORGANOBORANES

U2 - 10.1021/ol802651b

DO - 10.1021/ol802651b

M3 - Article (Academic Journal)

C2 - 19067552

SN - 1523-7060

VL - 11

SP - 165

EP - 168

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

Homologation of Boronic Esters with Lithiated Epoxides for the Stereocontrolled Synthesis of 1,2- and 1,3-Diols and 1,2,4-Triols

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Cite this