Catalytic asymmetric mannich-ketalization reaction: Highly enantioselective synthesis of aminobenzopyrans

Magnus Rueping; Ming Yuan Lin

doi:10.1002/chem.201000203

Catalytic asymmetric mannich-ketalization reaction: Highly enantioselective synthesis of aminobenzopyrans

Magnus Rueping^*, Ming Yuan Lin

^*Corresponding author for this work

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

103 Scopus citations

Abstract

"Chemical Equation Present" Domino catalysis: We have developed the first enantioselective domino Mannich-ketalization reaction of o-hydroxy benzaldimines with electron-rich alkenes (see scheme). The new reaction sequence provides an easy and direct access to optically pure 4-aminobenzopyrans in good yields and with excellent enantiomeric ratios (up to e.r. 98:2).

Original language	English (US)
Pages (from-to)	4169-4172
Number of pages	4
Journal	Chemistry - A European Journal
Volume	16
Issue number	14
DOIs	https://doi.org/10.1002/chem.201000203
State	Published - Apr 12 2010
Externally published	Yes

Keywords

Brønsted acid
Chromene
Domino reactions
Ion pairs
Organocatalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201000203

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title = "Catalytic asymmetric mannich-ketalization reaction: Highly enantioselective synthesis of aminobenzopyrans",

abstract = "{"}Chemical Equation Present{"} Domino catalysis: We have developed the first enantioselective domino Mannich-ketalization reaction of o-hydroxy benzaldimines with electron-rich alkenes (see scheme). The new reaction sequence provides an easy and direct access to optically pure 4-aminobenzopyrans in good yields and with excellent enantiomeric ratios (up to e.r. 98:2).",

keywords = "Br{\o}nsted acid, Chromene, Domino reactions, Ion pairs, Organocatalysis",

author = "Magnus Rueping and Lin, {Ming Yuan}",

year = "2010",

month = apr,

day = "12",

doi = "10.1002/chem.201000203",

language = "English (US)",

volume = "16",

pages = "4169--4172",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

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T1 - Catalytic asymmetric mannich-ketalization reaction

T2 - Highly enantioselective synthesis of aminobenzopyrans

AU - Rueping, Magnus

AU - Lin, Ming Yuan

PY - 2010/4/12

Y1 - 2010/4/12

N2 - "Chemical Equation Present" Domino catalysis: We have developed the first enantioselective domino Mannich-ketalization reaction of o-hydroxy benzaldimines with electron-rich alkenes (see scheme). The new reaction sequence provides an easy and direct access to optically pure 4-aminobenzopyrans in good yields and with excellent enantiomeric ratios (up to e.r. 98:2).

AB - "Chemical Equation Present" Domino catalysis: We have developed the first enantioselective domino Mannich-ketalization reaction of o-hydroxy benzaldimines with electron-rich alkenes (see scheme). The new reaction sequence provides an easy and direct access to optically pure 4-aminobenzopyrans in good yields and with excellent enantiomeric ratios (up to e.r. 98:2).

KW - Brønsted acid

KW - Chromene

KW - Domino reactions

KW - Ion pairs

KW - Organocatalysis

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U2 - 10.1002/chem.201000203

DO - 10.1002/chem.201000203

M3 - Article

C2 - 20309979

AN - SCOPUS:77950795873

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VL - 16

SP - 4169

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 14

ER -

Catalytic asymmetric mannich-ketalization reaction: Highly enantioselective synthesis of aminobenzopyrans

Abstract

Keywords

ASJC Scopus subject areas

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