Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

Panee C. Hutchison; Tom D. Heightman; David J. Procter

doi:10.1021/ol0268788

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

Panee C. Hutchison, Tom D. Heightman, David J. Procter

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

Abstract

(Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.

Original language	English
Pages (from-to)	4583-4585
Number of pages	2
Journal	Organic Letters
Volume	4
Issue number	26
DOIs	https://doi.org/10.1021/ol0268788
Publication status	Published - 26 Dec 2002

Keywords

Chiral auxiliary (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of amides contg. a resin-bound pseudoephedrine auxiliary as the key step); Asymmetric synthesis and induction; Solid phase synthesis (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Ketones Role: SPN (Synthetic preparation), PREP (Preparation) (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alcohols Role: SPN (Synthetic preparation), PREP (Preparation) (primary; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alkylation (stereoselective; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step)

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title = "Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase",

abstract = "(Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.",

keywords = "Chiral auxiliary (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of amides contg. a resin-bound pseudoephedrine auxiliary as the key step); Asymmetric synthesis and induction; Solid phase synthesis (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Ketones Role: SPN (Synthetic preparation), PREP (Preparation) (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alcohols Role: SPN (Synthetic preparation), PREP (Preparation) (primary; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step); Alkylation (stereoselective; enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of resin-bound pseudoephedrine amides as the key step)",

author = "Hutchison, {Panee C.} and Heightman, {Tom D.} and Procter, {David J.}",

year = "2002",

month = dec,

day = "26",

doi = "10.1021/ol0268788",

language = "English",

volume = "4",

pages = "4583--4585",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "26",

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TY - JOUR

T1 - Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

AU - Hutchison, Panee C.

AU - Heightman, Tom D.

AU - Procter, David J.

PY - 2002/12/26

Y1 - 2002/12/26

N2 - (Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.

AB - (Equation Presented) Immobilized pseudoephedrine amides have been conveniently prepared by attachment of pseudoephedrine to Merrifield resin and acylation on nitrogen. Deprotonation and alkylation of the resin bound amides proceeds smoothly. Products were cleaved from the resin to give ketones and alcohols in high enantiomeric excess and moderate to good overall yield.

KW - Chiral auxiliary (enantioselective prepn. of primary alcs. and ketones using enantioselective alkylation of amides contg. a resin-bound pseudoephedrine auxiliary as the key step); Asymmetric synthesis and induction; Solid phase synthesis (enantioselective

U2 - 10.1021/ol0268788

DO - 10.1021/ol0268788

M3 - Article

VL - 4

SP - 4583

EP - 4585

JO - Organic Letters

JF - Organic Letters

SN - 1523-7052

IS - 26

ER -

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

Abstract

Keywords

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