Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

D. Willcox; H. Gondal; M.G. Civit; Simon Woodward

doi:10.1016/j.tetlet.2014.01.105

Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

D. Willcox, H. Gondal, M.G. Civit, Simon Woodward

Inorganic Chemistry Group

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

Abstract

Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.

Original language	Undefined
Pages (from-to)	1720-1721
Number of pages	2
Journal	Tetrahedron Letters
Volume	55
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2014.01.105
Publication status	Published - 2014

Keywords

Hydroalumination
Conjugate addition
Alkenes
Michael reaction
Malonate

Access to Document

10.1016/j.tetlet.2014.01.105

Cite this

@article{b44a192fad364c17afcc40de7ec12b25,

title = "Assessing the utility of HAlCl2 derived vinylalanes for Michael addition",

abstract = "Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.",

keywords = "Hydroalumination, Conjugate addition, Alkenes, Michael reaction, Malonate",

author = "D. Willcox and H. Gondal and M.G. Civit and Simon Woodward",

year = "2014",

doi = "10.1016/j.tetlet.2014.01.105",

language = "Undefined",

volume = "55",

pages = "1720--1721",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier BV",

number = "10",

}

TY - JOUR

T1 - Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

AU - Willcox, D.

AU - Gondal, H.

AU - Civit, M.G.

AU - Woodward, Simon

PY - 2014

Y1 - 2014

N2 - Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.

AB - Rare alkenylalanes are prepared by Cp2TiCl2 or Cp*2ZrCl2 (Cp = η-C5H5; Cp* = η-C5Me5) catalysed addition of HAlCl2·(THF)2 to terminal alkynes (R1CCH; R1 = alkyl). Use of minimum head-volume sealed vials maximises the hydroalumination yields of volatile alkynes. Facile 1,4-addition of the resultant alkenylalanes to unsaturated malonates R2CHC(CO2R3)2 (R2 = alkyl, aryl, R3 = alkyl) is observed providing rapid and convenient access to the addition products.

KW - Hydroalumination

KW - Conjugate addition

KW - Alkenes

KW - Michael reaction

KW - Malonate

UR - http://www.scopus.com/inward/record.url?eid=2-s2.0-84896734290&partnerID=MN8TOARS

U2 - 10.1016/j.tetlet.2014.01.105

DO - 10.1016/j.tetlet.2014.01.105

M3 - Article

SN - 0040-4039

VL - 55

SP - 1720

EP - 1721

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Assessing the utility of HAlCl2 derived vinylalanes for Michael addition

Abstract

Keywords

Access to Document

Other files and links

Cite this