Aluminum triflate catalyzed tandem reactions of d -galactal: Toward chiral benzopyrans, chromenes, and chromans

Sandile B. Simelane; Henok H. Kinfe; Alfred Muller; D. Bradley G. Williams

doi:10.1021/ol502305j

Aluminum triflate catalyzed tandem reactions of d -galactal: Toward chiral benzopyrans, chromenes, and chromans

Sandile B. Simelane, Henok H. Kinfe, Alfred Muller, D. Bradley G. Williams

Chemical Sciences

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

23 Citations (Scopus)

Abstract

3,4,6-Tri-O-acetyl-d-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)₃ catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)₃/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.

Original language	English
Pages (from-to)	4543-4545
Number of pages	3
Journal	Organic Letters
Volume	16
Issue number	17
DOIs	https://doi.org/10.1021/ol502305j
Publication status	Published - 5 Sept 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Aluminum triflate catalyzed tandem reactions of d -galactal: Toward chiral benzopyrans, chromenes, and chromans",

abstract = "3,4,6-Tri-O-acetyl-d-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.",

author = "Simelane, {Sandile B.} and Kinfe, {Henok H.} and Alfred Muller and Williams, {D. Bradley G.}",

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AU - Simelane, Sandile B.

AU - Kinfe, Henok H.

AU - Muller, Alfred

AU - Williams, D. Bradley G.

PY - 2014/9/5

Y1 - 2014/9/5

N2 - 3,4,6-Tri-O-acetyl-d-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.

AB - 3,4,6-Tri-O-acetyl-d-galactal is selectively converted into 1-O-aryl-2-deoxy derivatives or chiral bridged benzopyrans under Al(OTf)3 catalysis, depending on reaction conditions. The benzopyrans react with Al(OTf)3/acetic anhydride in ring-opening reactions in the absence or presence of acetic acid to selectively produce chiral chromenes or chromans, respectively, in high yields.

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ER -

Aluminum triflate catalyzed tandem reactions of d -galactal: Toward chiral benzopyrans, chromenes, and chromans

Abstract

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