Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

Magnus Rueping; Estíbaliz Merino; Michael Bolte

doi:10.1039/c2ob25443c

Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

Magnus Rueping^*, Estíbaliz Merino, Michael Bolte

^*Corresponding author for this work

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

17 Scopus citations

Abstract

A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

Original language	English (US)
Pages (from-to)	6201-6210
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	30
DOIs	https://doi.org/10.1039/c2ob25443c
State	Published - Aug 14 2012
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c2ob25443c

Cite this

@article{b59c98a4a6da477ab86e8c748a3aad42,

title = "Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives",

abstract = "A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.",

author = "Magnus Rueping and Est{\'i}baliz Merino and Michael Bolte",

year = "2012",

month = aug,

day = "14",

doi = "10.1039/c2ob25443c",

language = "English (US)",

volume = "10",

pages = "6201--6210",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "30",

}

TY - JOUR

T1 - Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

AU - Rueping, Magnus

AU - Merino, Estíbaliz

AU - Bolte, Michael

PY - 2012/8/14

Y1 - 2012/8/14

N2 - A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

AB - A highly efficient route for the synthesis of valuable 3,4-substituted chromenone derivatives by the reaction of 1,3-diketones with aldehydes in the presence of l-proline was developed. The reactions take advantage of readily available starting materials and follow a Knoevenagel condensation/Michael addition/hemiacetalization domino process. Chiral 3-substituted chromenones are obtained with high enantioselectivities when a chiral diarylprolinol TMS-ether is applied in the reaction.

UR - http://www.scopus.com/inward/record.url?scp=84863963314&partnerID=8YFLogxK

U2 - 10.1039/c2ob25443c

DO - 10.1039/c2ob25443c

M3 - Article

C2 - 22585353

AN - SCOPUS:84863963314

SN - 1477-0520

VL - 10

SP - 6201

EP - 6210

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 30

ER -

Efficient proline and prolinol ether mediated 3-component synthesis of 3- and 3,4-substituted chromenone derivatives

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this