Lithiation and reactions of stilbene oxides: Synthetic utility

Saverio Florio; Varinder K Aggarwal; Antonio Salomone

doi:10.1021/ol0485013

Lithiation and reactions of stilbene oxides: Synthetic utility

Saverio Florio, Varinder K Aggarwal, Antonio Salomone

School of Chemistry

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

40 Citations (Scopus)

Abstract

The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

Translated title of the contribution	Lithiation and Reactions of Stilbene Oxides: Synthetic Utility
Original language	English
Pages (from-to)	4191-4194
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	23
DOIs	https://doi.org/10.1021/ol0485013
Publication status	Published - 11 Nov 2004

Keywords

STEREOSPECIFIC SYNTHESIS
OXIRANYL ANION
STEREOSELECTIVE SYNTHESIS
METALATED EPOXIDES
CARBONYL-COMPOUNDS
ORGANIC-SYNTHESIS
HEMIBREVETOXIN B
OXAZOLINYLOXIRANES
EPOXIDATION
CYCLIZATION

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title = "Lithiation and reactions of stilbene oxides: Synthetic utility",

abstract = "The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.",

keywords = "STEREOSPECIFIC SYNTHESIS, OXIRANYL ANION, STEREOSELECTIVE SYNTHESIS, METALATED EPOXIDES, CARBONYL-COMPOUNDS, ORGANIC-SYNTHESIS, HEMIBREVETOXIN B, OXAZOLINYLOXIRANES, EPOXIDATION, CYCLIZATION",

author = "Saverio Florio and Aggarwal, {Varinder K} and Antonio Salomone",

year = "2004",

month = nov,

day = "11",

doi = "10.1021/ol0485013",

language = "English",

volume = "6",

pages = "4191--4194",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Lithiation and reactions of stilbene oxides

T2 - Synthetic utility

AU - Florio, Saverio

AU - Aggarwal, Varinder K

AU - Salomone, Antonio

PY - 2004/11/11

Y1 - 2004/11/11

N2 - The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

AB - The lithiation of trans- and cis-stilbene oxides (+/-)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (+/-)-1, ortho-lithiation competed with alpha-lithiation depending upon the experimental conditions. The configurational stability of the alpha-lithiated cis- and trans-stilbene oxides (+/-)-2 and (+/-)-9, respectively, was proved as well as that of scalemic stilbene oxide (R,R)-2.

KW - STEREOSPECIFIC SYNTHESIS

KW - OXIRANYL ANION

KW - STEREOSELECTIVE SYNTHESIS

KW - METALATED EPOXIDES

KW - CARBONYL-COMPOUNDS

KW - ORGANIC-SYNTHESIS

KW - HEMIBREVETOXIN B

KW - OXAZOLINYLOXIRANES

KW - EPOXIDATION

KW - CYCLIZATION

U2 - 10.1021/ol0485013

DO - 10.1021/ol0485013

M3 - Article (Academic Journal)

SN - 1523-7060

VL - 6

SP - 4191

EP - 4194

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Lithiation and reactions of stilbene oxides: Synthetic utility

Abstract

Keywords

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