Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Oleksandr Zhurakovskyi; Rafael M.P. Dias; Adam Noble; Varinder K. Aggarwal

doi:10.1021/acs.orglett.8b01252

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Oleksandr Zhurakovskyi, Rafael M.P. Dias, Adam Noble, Varinder K. Aggarwal^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

10 Citations (Scopus)

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Abstract

A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

Original language	English
Pages (from-to)	3136-3139
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	10
Early online date	9 May 2018
DOIs	https://doi.org/10.1021/acs.orglett.8b01252
Publication status	Published - 18 May 2018

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10.1021/acs.orglett.8b01252

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This is the final published version of the article (version of record). It first appeared online via ACS at https://doi.org/10.1021/acs.orglett.8b01252 . Please refer to any applicable terms of use of the publisher.
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Cite this

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title = "Stereo- and Regiocontrolled Methylboration of Terminal Alkynes",

abstract = "A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.",

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T1 - Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

AU - Zhurakovskyi, Oleksandr

AU - Dias, Rafael M.P.

AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2018/5/18

Y1 - 2018/5/18

N2 - A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

AB - A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.

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Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Abstract

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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this

Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

Abstract

Access to Document

Other files and links

Fingerprint

Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Cite this