Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

Vijaya Lingam Manthati; A. Sai Krishna Murthy; Frédéric Caijo; Delphine Drouin; Philippe Lesot; Danielle Grée; René Grée

doi:10.1016/j.tetasy.2006.08.010

Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

Vijaya Lingam Manthati, A. Sai Krishna Murthy, Frédéric Caijo, Delphine Drouin, Philippe Lesot, Danielle Grée, René Grée

Biochemistry

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

17 Scopus citations

Abstract

The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's >95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules.

Original language	English (US)
Pages (from-to)	2306-2310
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	15
DOIs	https://doi.org/10.1016/j.tetasy.2006.08.010
State	Published - Sep 11 2006

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2006.08.010

Cite this

@article{8e77920ca1ad46b3b77141e536755ed1,

title = "Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate",

abstract = "The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's >95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules.",

author = "Manthati, {Vijaya Lingam} and {Sai Krishna Murthy}, A. and Fr{\'e}d{\'e}ric Caijo and Delphine Drouin and Philippe Lesot and Danielle Gr{\'e}e and Ren{\'e} Gr{\'e}e",

note = "Funding Information: We thank Dr. Michael Prakesch for preliminary experiments in these series and Dr. Virginie Vidal for very fruitful discussions on the use of Noyori{\textquoteright}s catalyst. A. S. K. Murthy thanks the French MENRT for a post-doctoral fellowship. We thank CNRS and MENRT for financial support.",

year = "2006",

month = sep,

day = "11",

doi = "10.1016/j.tetasy.2006.08.010",

language = "English (US)",

volume = "17",

pages = "2306--2310",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "15",

}

TY - JOUR

T1 - Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

AU - Manthati, Vijaya Lingam

AU - Sai Krishna Murthy, A.

AU - Caijo, Frédéric

AU - Drouin, Delphine

AU - Lesot, Philippe

AU - Grée, Danielle

AU - Grée, René

N1 - Funding Information: We thank Dr. Michael Prakesch for preliminary experiments in these series and Dr. Virginie Vidal for very fruitful discussions on the use of Noyori’s catalyst. A. S. K. Murthy thanks the French MENRT for a post-doctoral fellowship. We thank CNRS and MENRT for financial support.

PY - 2006/9/11

Y1 - 2006/9/11

N2 - The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's >95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules.

AB - The asymmetric synthesis of propargylic fluorides, (+)-6 and (+)-3 with ee's >95%, is reported. The first key step involves an asymmetric transfer hydrogenation of the propargylic ketone 11, using Noyori's catalyst, to give alcohol (+)-10. The second important step is the highly stereoselective DAST mediated fluorination of the propargylic alcohol (-)-5. The ee determinations were performed using both NMR in chiral solvents and chiral GC. These propargylic fluorides appear to be useful intermediates in the preparation of fluorinated analogues of bioactive chiral molecules.

UR - http://www.scopus.com/inward/record.url?scp=33748710818&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33748710818&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2006.08.010

DO - 10.1016/j.tetasy.2006.08.010

M3 - Article

AN - SCOPUS:33748710818

SN - 0957-4166

VL - 17

SP - 2306

EP - 2310

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 15

ER -

Enantioselective synthesis of methyl-5(R)-fluorohept-6-ynoate

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this