CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES

D S  BROWN; P T  GALLAGHER; A P  LIGHTFOOT; C J  MOODY; A M Z  SLAWIN; E  SWANN

CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES

D S BROWN
, P T GALLAGHER
, A P LIGHTFOOT
, C J MOODY
, A M Z SLAWIN
, E SWANN

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

Abstract

Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84% yield with up to 95% diastereomeric excess.

Original language	English
Pages (from-to)	11473-11488
Number of pages	16
Journal	Tetrahedron
Volume	51
Issue number	42
Publication status	Published - 16 Oct 1995

Keywords

ALDEHYDE-SAMP HYDRAZONES
ALPHA-IMINO ESTERS
SODIUM-BOROHYDRIDE
ORGANOLITHIUM REAGENTS
AMINO-ACIDS
ETHERS
REDUCTION
CHLORIDE

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@article{031a0edcf7ab4cbfab2590d9c606623c,

title = "CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES",

abstract = "Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84\% yield with up to 95\% diastereomeric excess.",

keywords = "ALDEHYDE-SAMP HYDRAZONES, ALPHA-IMINO ESTERS, SODIUM-BOROHYDRIDE, ORGANOLITHIUM REAGENTS, AMINO-ACIDS, ETHERS, REDUCTION, CHLORIDE",

author = "BROWN, \{D S\} and GALLAGHER, \{P T\} and LIGHTFOOT, \{A P\} and MOODY, \{C J\} and SLAWIN, \{A M Z\} and E SWANN",

year = "1995",

month = oct,

day = "16",

language = "English",

volume = "51",

pages = "11473--11488",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "42",

}

TY - JOUR

T1 - CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES

AU - BROWN, D S

AU - GALLAGHER, P T

AU - LIGHTFOOT, A P

AU - MOODY, C J

AU - SLAWIN, A M Z

AU - SWANN, E

PY - 1995/10/16

Y1 - 1995/10/16

N2 - Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84% yield with up to 95% diastereomeric excess.

AB - Addition of Grignard and organolithium reagents to O-(1-phenylethyl) aldoximes in the presence of boron trifluoride etherate gives secondary hydroxylamines in 21-84% yield with up to 95% diastereomeric excess.

KW - ALDEHYDE-SAMP HYDRAZONES

KW - ALPHA-IMINO ESTERS

KW - SODIUM-BOROHYDRIDE

KW - ORGANOLITHIUM REAGENTS

KW - AMINO-ACIDS

KW - ETHERS

KW - REDUCTION

KW - CHLORIDE

M3 - Article

SN - 0040-4020

VL - 51

SP - 11473

EP - 11488

JO - Tetrahedron

JF - Tetrahedron

IS - 42

ER -

CHIRAL OXIMES IN ASYMMETRIC-SYNTHESIS - ADDITION OF ORGANOMETALLIC REAGENTS TO O-(1-PHENYLETHYL) ALDOXIMES

Abstract

Keywords

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