Selective Synthesis of Silacycles by Borane-Catalyzed Domino Hydrosilylation of Proximal Unsaturated Bonds: Tunable Approach to 1,n-Diols

Cited 8 time in webofscience Cited 0 time in scopus
  • Hit : 351
  • Download : 0
The tris(pentafluorophenyl)boron-catalyzed domino hydrosilylation of substrates carrying unsaturated functionalities in a proximal arrangement is presented to produce silacycles. Excellent levels of efficiency and selectivity were achieved in the cyclization by the deliberate choice of the hydrosilane reagents. The key to successful cyclic hydrosilylation is the reactivity enhancement of the second intramolecular hydrosilylation by a proximity effect. Not only dienes but also enones, enynes, ynones and enimines readily afford medium-sized silacycles under convenient and mild conditions. The cyclization proceeds with acceptable diastereoselectivity mainly controlled by the conformational bias towards inducing additional stereogenic centers. The silacycles obtained from this reaction were converted to 1,n-diols or 1,n-amino alcohols upon oxidation, thus rendering the present cyclization a powerful tool for accessing synthetically valuable building blocks.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2017-10
Language
English
Article Type
Article
Keywords

ASYMMETRIC DIHYDROXYLATION; INTRAMOLECULAR HYDROSILYLATION; CYCLIC HYDROBORATION; B(C6F5)(3)-CATALYZED HYDROSILATION; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ORGANOSILICON COMPOUNDS; RING-CLOSURE; MECHANISM; OLEFINS

Citation

ADVANCED SYNTHESIS & CATALYSIS, v.359, no.19, pp.3428 - 3436

ISSN
1615-4150
DOI
10.1002/adsc.201700698
URI
http://hdl.handle.net/10203/226712
Appears in Collection
CH-Journal Papers(저널논문)
Files in This Item
There are no files associated with this item.
This item is cited by other documents in WoS
⊙ Detail Information in WoSⓡ Click to see webofscience_button
⊙ Cited 8 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0