Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

D. R. Boyd; N. D. Sharma; M. Kaik; M. Bell; M. V. Berberian; P.B.A. McIntyre; B. Kelly; C. Hardacre; P. J. Stevenson; C. C. R. Allen

doi:10.1002/adsc.201100273

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

D. R. Boyd, N. D. Sharma, M. Kaik, M. Bell, M. V. Berberian, P.B.A. McIntyre, B. Kelly, C. Hardacre, P. J. Stevenson, C. C. R. Allen

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

9 Citations (Scopus)

Abstract

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.

Original language	English
Pages (from-to)	2455-2465
Number of pages	11
Journal	Advanced Synthesis & Catalysis
Volume	353
Issue number	13
DOIs	https://doi.org/10.1002/adsc.201100273
Publication status	Published - Sept 2011

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201100273

Cite this

Boyd, D. R., Sharma, N. D., Kaik, M., Bell, M., Berberian, M. V., McIntyre, P. B. A., Kelly, B., Hardacre, C., Stevenson, P. J., & Allen, C. C. R. (2011). Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles. Advanced Synthesis & Catalysis, 353(13), 2455-2465. https://doi.org/10.1002/adsc.201100273

@article{7521951e7625453e9809d14f0b31095d,

title = "Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles",

abstract = "Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.",

author = "Boyd, {D. R.} and Sharma, {N. D.} and M. Kaik and M. Bell and Berberian, {M. V.} and P.B.A. McIntyre and B. Kelly and C. Hardacre and Stevenson, {P. J.} and Allen, {C. C. R.}",

year = "2011",

month = sep,

doi = "10.1002/adsc.201100273",

language = "English",

volume = "353",

pages = "2455--2465",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "13",

}

TY - JOUR

T1 - Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

AU - Boyd, D. R.

AU - Sharma, N. D.

AU - Kaik, M.

AU - Bell, M.

AU - Berberian, M. V.

AU - McIntyre, P.B.A.

AU - Kelly, B.

AU - Hardacre, C.

AU - Stevenson, P. J.

AU - Allen, C. C. R.

PY - 2011/9

Y1 - 2011/9

N2 - Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.

AB - Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.

U2 - 10.1002/adsc.201100273

DO - 10.1002/adsc.201100273

M3 - Article

SN - 1615-4150

VL - 353

SP - 2455

EP - 2465

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 13

ER -

Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

Abstract

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this