Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade

Magnus Rueping; Lukas Hubener

doi:10.1055/s-0030-1259955

Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade

Magnus Rueping^*, Lukas Hubener

^*Corresponding author for this work

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

37 Scopus citations

Abstract

A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities.

Original language	English (US)
Article number	Y03411ST
Pages (from-to)	1243-1246
Number of pages	4
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-0030-1259955
State	Published - 2011
Externally published	Yes

Keywords

Hantzsch ester
amines
asymmetric reduction
domino reaction
organocatalysis

ASJC Scopus subject areas

Organic Chemistry

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title = "Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade",

abstract = "A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities.",

keywords = "Hantzsch ester, amines, asymmetric reduction, domino reaction, organocatalysis",

author = "Magnus Rueping and Lukas Hubener",

year = "2011",

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language = "English (US)",

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journal = "Synlett",

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AU - Rueping, Magnus

AU - Hubener, Lukas

PY - 2011

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N2 - A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities.

AB - A catalytic enantioselective synthesis of a new class of quinolizidines and indolizidines is presented. An asymmetric Bronsted acid catalyzed hydrogenation cascade as well as a sequential Bronsted acid/metal catalyzed hydrogenation protocol of 2-substituted quinolines yields benzofused quinolizidines and indolizidines in good yields with high diastereo- and enantioselectivities.

KW - Hantzsch ester

KW - amines

KW - asymmetric reduction

KW - domino reaction

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=79957483083&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1259955

DO - 10.1055/s-0030-1259955

M3 - Article

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M1 - Y03411ST

ER -

Enantioselective synthesis of quinolizidines and indolizidines via a catalytic asymmetric hydrogenation cascade

Abstract

Keywords

ASJC Scopus subject areas

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