Asymmetrie organocatalytic cyclopropanation - Highly stereocontrolled synthesis of chiral cyclopropanes with quaternary stereocenters

Xavier Companyó; Andrea Nekane Alba; Francisco Cárdenas; Albert Moyano; Ramon Rios

doi:10.1002/ejoc.200900209

Asymmetrie organocatalytic cyclopropanation - Highly stereocontrolled synthesis of chiral cyclopropanes with quaternary stereocenters

Xavier Companyó
, Andrea Nekane Alba
, Francisco Cárdenas
, Albert Moyano
, Ramon Rios

Chemistry

Universitat de Barcelona

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

82 Scopus citations

Abstract

A convenient and novel domino reaction for the synthesis of highly functionalized cyclopropanes is reported. The addition of 2-bromoketo estere to a variety of α, β-unsaturated aldehydes catalyzed by secondary amines leads to chiral cyclopropanes with three stereogenic carbon atoms, including one quaternary Stereocenter, in a highly stereocontrolled fashion.

Original language	British English
Pages (from-to)	3075-3080
Number of pages	6
Journal	European Journal of Organic Chemistry
Issue number	18
DOIs	https://doi.org/10.1002/ejoc.200900209
State	Published - Jun 2009

Keywords

Cyclopropanation
Diastereoselectivity
Enantioselectivity
Organocatalysis
Quaternary centers

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10.1002/ejoc.200900209

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title = "Asymmetrie organocatalytic cyclopropanation - Highly stereocontrolled synthesis of chiral cyclopropanes with quaternary stereocenters",

abstract = "A convenient and novel domino reaction for the synthesis of highly functionalized cyclopropanes is reported. The addition of 2-bromoketo estere to a variety of α, β-unsaturated aldehydes catalyzed by secondary amines leads to chiral cyclopropanes with three stereogenic carbon atoms, including one quaternary Stereocenter, in a highly stereocontrolled fashion.",

keywords = "Cyclopropanation, Diastereoselectivity, Enantioselectivity, Organocatalysis, Quaternary centers",

author = "Xavier Company{\'o} and Alba, \{Andrea Nekane\} and Francisco C{\'a}rdenas and Albert Moyano and Ramon Rios",

year = "2009",

month = jun,

doi = "10.1002/ejoc.200900209",

language = "British English",

pages = "3075--3080",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "18",

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TY - JOUR

T1 - Asymmetrie organocatalytic cyclopropanation - Highly stereocontrolled synthesis of chiral cyclopropanes with quaternary stereocenters

AU - Companyó, Xavier

AU - Alba, Andrea Nekane

AU - Cárdenas, Francisco

AU - Moyano, Albert

AU - Rios, Ramon

PY - 2009/6

Y1 - 2009/6

N2 - A convenient and novel domino reaction for the synthesis of highly functionalized cyclopropanes is reported. The addition of 2-bromoketo estere to a variety of α, β-unsaturated aldehydes catalyzed by secondary amines leads to chiral cyclopropanes with three stereogenic carbon atoms, including one quaternary Stereocenter, in a highly stereocontrolled fashion.

AB - A convenient and novel domino reaction for the synthesis of highly functionalized cyclopropanes is reported. The addition of 2-bromoketo estere to a variety of α, β-unsaturated aldehydes catalyzed by secondary amines leads to chiral cyclopropanes with three stereogenic carbon atoms, including one quaternary Stereocenter, in a highly stereocontrolled fashion.

KW - Cyclopropanation

KW - Diastereoselectivity

KW - Enantioselectivity

KW - Organocatalysis

KW - Quaternary centers

UR - https://www.scopus.com/pages/publications/66749088008

U2 - 10.1002/ejoc.200900209

DO - 10.1002/ejoc.200900209

M3 - Article

AN - SCOPUS:66749088008

SN - 1434-193X

SP - 3075

EP - 3080

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 18

ER -

Asymmetrie organocatalytic cyclopropanation - Highly stereocontrolled synthesis of chiral cyclopropanes with quaternary stereocenters

Abstract

Keywords

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