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Phosphazene catalyzed addition to electron-deficient alkynes: the importance of non-linear allenyl intermediates upon stereoselectivity.

Abstract:

An ONIOM QM/MM study on the mechanism of the Michael addition to triple bonds catalyzed by chiral diiminophosphorane catalysts has been performed to understand the stereoselectivity of the product olefin. Our results are consistent with the experimental enantioselectivity, but more importantly, reveal that the Z vs E preference depends on the influence of the catalyst upon the geometry of the allenyl enolate formed in the addition step. These intermediates show an innate preference for a (Z)-...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.7b00540

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Institution:
University of Oxford
Oxford college:
St Hilda's College
Role:
Author
Publisher:
American Chemical Society Publisher's website
Journal:
Journal of Organic Chemistry Journal website
Volume:
82
Issue:
7
Pages:
3855–3863
Publication date:
2017-03-01
Acceptance date:
2017-03-16
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Source identifiers:
686929
Language:
English
Keywords:
Pubs id:
pubs:686929
UUID:
uuid:784812e1-b4e5-4d0d-9472-a9b11ef0e93a
Local pid:
pubs:686929
Deposit date:
2017-03-31

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