Telescoped Synthesis of Stereodefined Pyrrolidines

Dorine Belmessieri; David B. Cordes; Alexandra Martha Zoya Slawin; Andrew David Smith

doi:10.1021/ol401554y

Telescoped Synthesis of Stereodefined Pyrrolidines

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Abstract

Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99% ee) have been developed using commercially available tetramisole (0.1 to 5 mol %). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.

Original language	English
Pages (from-to)	3472-3475
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	13
Early online date	25 Jun 2013
DOIs	https://doi.org/10.1021/ol401554y
Publication status	Published - 2013

Keywords

CATALYZED ALDOL-LACTONIZATION
TRICYCLIC BETA-LACTONES
ASYMMETRIC-SYNTHESIS
KINETIC RESOLUTION
CONJUGATE ADDITION
ACID
BENZOTETRAMISOLE
ORGANOCATALYSIS
CYCLOADDITION
ALKALOIDS

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Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation
Belmessieri, D. (Author), Smith, A. (Supervisor), 25 Jun 2014
Student thesis: Doctoral Thesis (PhD)

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@article{b186973151f74504bb56987acbba216b,

title = "Telescoped Synthesis of Stereodefined Pyrrolidines",

abstract = "Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99\% ee) have been developed using commercially available tetramisole (0.1 to 5 mol \%). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.",

keywords = "CATALYZED ALDOL-LACTONIZATION, TRICYCLIC BETA-LACTONES, ASYMMETRIC-SYNTHESIS, KINETIC RESOLUTION, CONJUGATE ADDITION, ACID, BENZOTETRAMISOLE, ORGANOCATALYSIS, CYCLOADDITION, ALKALOIDS",

author = "Dorine Belmessieri and Cordes, \{David B.\} and Slawin, \{Alexandra Martha Zoya\} and Smith, \{Andrew David\}",

year = "2013",

doi = "10.1021/ol401554y",

language = "English",

volume = "15",

pages = "3472--3475",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "13",

}

TY - JOUR

T1 - Telescoped Synthesis of Stereodefined Pyrrolidines

AU - Belmessieri, Dorine

AU - Cordes, David B.

AU - Slawin, Alexandra Martha Zoya

AU - Smith, Andrew David

PY - 2013

Y1 - 2013

N2 - Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99% ee) have been developed using commercially available tetramisole (0.1 to 5 mol %). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.

AB - Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99% ee) have been developed using commercially available tetramisole (0.1 to 5 mol %). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.

KW - CATALYZED ALDOL-LACTONIZATION

KW - TRICYCLIC BETA-LACTONES

KW - ASYMMETRIC-SYNTHESIS

KW - KINETIC RESOLUTION

KW - CONJUGATE ADDITION

KW - ACID

KW - BENZOTETRAMISOLE

KW - ORGANOCATALYSIS

KW - CYCLOADDITION

KW - ALKALOIDS

U2 - 10.1021/ol401554y

DO - 10.1021/ol401554y

M3 - Article

SN - 1523-7060

VL - 15

SP - 3472

EP - 3475

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Telescoped Synthesis of Stereodefined Pyrrolidines

Abstract

Keywords

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Student theses

Applications of isothioureas in organocatalysis: kinetic resolution of secondary alcohols and intramolecular Michael addition-lactonisation

Cite this