Angewandte
Chemie
cyclic compounds after subsequent appropriate transforma-
tions.
Received: August 30, 2006
Revised: October 18, 2006
Published online: January 4, 2007
Keywords: asymmetric catalysis · enynes ·
.
hydrosilylation/cyclization · P ligands · rhodium
Scheme 2. Examples for the conversion of the silyl groups of the
silylcyclization products. TBAF=tetrabutylammonium fluoride.
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Figure 1. Proposed model for the stereoselectivity in the silylcyclization
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reactions.
Figure 1. In TS-1 the bulky silyl groupis located in a relatively
open area; this orientation favors the formation of the S
product, which is consistent with the absolute configuration of
(S)-3ca determined by X-ray analysis.
In conclusion, we have developed an efficient catalyst,
namely the rhodium complex of spiro diphosphine SDP, for
the asymmetric silylcyclization of 1,6-enynes. This highly
enantioselective reaction provides a facile access to optically
active silylalkylidene cyclopentane and pyrrolidine deriva-
tives, along with other functionalized carbocyclic and hetero-
Angew. Chem. Int. Ed. 2007, 46, 1275 –1277
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