Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions

Chihliang Chang; Ssu Hsien Li; Raju Jannapu Reddy; Kwunmin Chen

doi:10.1002/adsc.200800771

Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions

Chihliang Chang
, Ssu Hsien Li
, Raju Jannapu Reddy
, Kwunmin Chen^*

^*Corresponding author for this work

Department of Chemistry

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

68 Citations (Scopus)

Abstract

A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α-disubstituted aldehydes with β-nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).

Original language	English
Pages (from-to)	1273-1278
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	351
Issue number	9
DOIs	https://doi.org/10.1002/adsc.200800771
Publication status	Published - 2009 Jun

Keywords

Asymmetric catalysis
Michael reaction
Quaternary carbon centers
Solventfree reaction
β-nitroalkenes

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.200800771

Fingerprint

Dive into the research topics of 'Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions'. Together they form a unique fingerprint.

Cite this

Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions. / Chang, Chihliang; Li, Ssu Hsien; Reddy, Raju Jannapu et al.
In: Advanced Synthesis and Catalysis, Vol. 351, No. 9, 06.2009, p. 1273-1278.

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

Chang, C, Li, SH, Reddy, RJ & Chen, K 2009, 'Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions', Advanced Synthesis and Catalysis, vol. 351, no. 9, pp. 1273-1278. https://doi.org/10.1002/adsc.200800771

@article{3ff54655317d429fa288f2682d687dcb,

title = "Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions",

abstract = "A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α-disubstituted aldehydes with β-nitroalkenes in the presence of 20 mol\% organocatalyst 3 and 20 mol\% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99\% yield) and high levels of enantioselectivities (up to 95\% ee).",

keywords = "Asymmetric catalysis, Michael reaction, Quaternary carbon centers, Solventfree reaction, β-nitroalkenes",

author = "Chihliang Chang and Li, \{Ssu Hsien\} and Reddy, \{Raju Jannapu\} and Kwunmin Chen",

year = "2009",

month = jun,

doi = "10.1002/adsc.200800771",

language = "English",

volume = "351",

pages = "1273--1278",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "9",

}

TY - JOUR

T1 - Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes

T2 - Construction of quaternary carbon-bearing aldehydes under solvent-free conditions

AU - Chang, Chihliang

AU - Li, Ssu Hsien

AU - Reddy, Raju Jannapu

AU - Chen, Kwunmin

PY - 2009/6

Y1 - 2009/6

N2 - A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α-disubstituted aldehydes with β-nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).

AB - A novel pyrrolidine-camphor organocatalyst 3 was designed, synthesized and proven to be an efficient catalyst for the asymmetric Michael reaction. Treatment of α,α-disubstituted aldehydes with β-nitroalkenes in the presence of 20 mol% organocatalyst 3 and 20 mol% benzoic acid under solvent-free conditions provided the desired Michael product possessing an all-carbon quaternary center with high chemical yields (up to 99% yield) and high levels of enantioselectivities (up to 95% ee).

KW - Asymmetric catalysis

KW - Michael reaction

KW - Quaternary carbon centers

KW - Solventfree reaction

KW - β-nitroalkenes

UR - https://www.scopus.com/pages/publications/67549084539

UR - https://www.scopus.com/pages/publications/67549084539#tab=citedBy

U2 - 10.1002/adsc.200800771

DO - 10.1002/adsc.200800771

M3 - Article

AN - SCOPUS:67549084539

SN - 1615-4150

VL - 351

SP - 1273

EP - 1278

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 9

ER -

Pyrrolidine-camphor derivative as an organocatalyst for asymmetic michael additions of α,α-disubstituted aldehydes to β-nitroalkenes: Construction of quaternary carbon-bearing aldehydes under solvent-free conditions

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this