Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins

Hui Jin; Soo Min Cho; Geum Sook Hwang; Do Hyun Ryu

doi:10.1002/adsc.201600825

Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins

Hui Jin, Soo Min Cho, Geum Sook Hwang, Do Hyun Ryu

Department of Chemistry

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

17 Scopus citations

Abstract

An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr, and >99% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).

Original language	English
Pages (from-to)	163-167
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	1
DOIs	https://doi.org/10.1002/adsc.201600825
State	Published - 4 Jan 2017

Keywords

3,4-dihydrocoumarins
L-proline
Michael addition
organocatalysis
quaternary

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title = "Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins",

abstract = "An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99\% yield, >20:1 dr, and >99\% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).",

keywords = "3,4-dihydrocoumarins, L-proline, Michael addition, organocatalysis, quaternary",

author = "Hui Jin and Cho, \{Soo Min\} and Hwang, \{Geum Sook\} and Ryu, \{Do Hyun\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = jan,

day = "4",

doi = "10.1002/adsc.201600825",

language = "English",

volume = "359",

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publisher = "Wiley-VCH Verlag",

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Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins. / Jin, Hui; Cho, Soo Min; Hwang, Geum Sook et al.
In: Advanced Synthesis and Catalysis, Vol. 359, No. 1, 04.01.2017, p. 163-167.

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

TY - JOUR

T1 - Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters

T2 - Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins

AU - Jin, Hui

AU - Cho, Soo Min

AU - Hwang, Geum Sook

AU - Ryu, Do Hyun

PY - 2017/1/4

Y1 - 2017/1/4

N2 - An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr, and >99% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).

AB - An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr, and >99% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).

KW - 3,4-dihydrocoumarins

KW - L-proline

KW - Michael addition

KW - organocatalysis

KW - quaternary

UR - https://www.scopus.com/pages/publications/85006782909

U2 - 10.1002/adsc.201600825

DO - 10.1002/adsc.201600825

M3 - Article

AN - SCOPUS:85006782909

SN - 1615-4150

VL - 359

SP - 163

EP - 167

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 1

ER -

Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins

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Keywords

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