Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes

Ying Fang Ting, Chihliang Chang, Raju Jannapu Reddy, Dhananjay R. Magar, Kwunmin Chen

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.

Original languageEnglish
Pages (from-to)7030-7038
Number of pages9
JournalChemistry - A European Journal
Volume16
Issue number23
DOIs
Publication statusPublished - 2010 Jun 18

Fingerprint

Camphor
Stereoselectivity
Ketones
Aldehydes
Derivatives
Catalysts
Cyclohexane
citronellal

Keywords

  • Camphor
  • Citronellal
  • Michael addition
  • Nitroalkenes
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

Cite this

Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes. / Ting, Ying Fang; Chang, Chihliang; Reddy, Raju Jannapu; Magar, Dhananjay R.; Chen, Kwunmin.

In: Chemistry - A European Journal, Vol. 16, No. 23, 18.06.2010, p. 7030-7038.

Research output: Contribution to journalArticle

@article{435aa9ec765e41139e5d6c7e471a1b3c,
title = "Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes",
abstract = "Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99{\%} enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.",
keywords = "Camphor, Citronellal, Michael addition, Nitroalkenes, Organocatalysis",
author = "Ting, {Ying Fang} and Chihliang Chang and Reddy, {Raju Jannapu} and Magar, {Dhananjay R.} and Kwunmin Chen",
year = "2010",
month = "6",
day = "18",
doi = "10.1002/chem.201000483",
language = "English",
volume = "16",
pages = "7030--7038",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "23",

}

TY - JOUR

T1 - Pyrrolidinyl-camphor derivatives as a new class of organocatalyst for direct asymmetric Michael addition of aldehydes and ketones to β-nitroalkenes

AU - Ting, Ying Fang

AU - Chang, Chihliang

AU - Reddy, Raju Jannapu

AU - Magar, Dhananjay R.

AU - Chen, Kwunmin

PY - 2010/6/18

Y1 - 2010/6/18

N2 - Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.

AB - Practical and convenient synthetic routes have been developed for the synthesis of a new class of pyrrolidinyl-camphor derivatives (7a-h). These novel compounds were screened as catalysts for the direct Michael addition of symmetrical αα-disubstituted aldehydes to β-nitroalkenes. When this asymmetric transformation was cata-lyzed by organocatalyst 7f, the desired Michael adducts were obtained in high chemical yields, with high to excellent stereoselectivities (up to 98:2 diaste-reomeric ratio (d.r.) and 99% enantiomeric excess (ee)). The scope of the catalytic system was expanded to encompass various aldehydes and ketones as the donor sources. The synthetic application was demonstrated by the synthesis of a tetrasubstituted-cyclohexane derivative from (S)-citronellal, with high stereoselectivity.

KW - Camphor

KW - Citronellal

KW - Michael addition

KW - Nitroalkenes

KW - Organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=77953563112&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77953563112&partnerID=8YFLogxK

U2 - 10.1002/chem.201000483

DO - 10.1002/chem.201000483

M3 - Article

C2 - 20455225

AN - SCOPUS:77953563112

VL - 16

SP - 7030

EP - 7038

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 23

ER -