TY - JOUR
T1 - A trans-chelating bisphosphine possessing only planar chirality and its application to catalytic asymmetric reactions
AU - Kuwano, Ryoichi
AU - Uemura, Takashi
AU - Saitoh, Makoto
AU - Ito, Yoshihiko
N1 - Funding Information:
This work was partly supported by a Grant-in-Aid for Scientific Research on Priority Areas, No. 706: Dynamic Control of Stereochemistry, from the Ministry of Education, Science, Sports, and Culture.
PY - 2004/7/26
Y1 - 2004/7/26
N2 - A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.
AB - A new chiral bisphosphine, (S,S)-2,2″-bis[(diethylphosphino)methyl]- 1,1″-biferrocene [(S,S)-EtTRAP-H], was synthesized in seven steps in 45% overall yield from ferrocenyloxazoline derived from (S)-valinol. The new chiral phosphine has only planar chirality, and is able to form a trans-chelate metal complex. (S,S)-EtTRAP-H is an effective ligand in rhodium-catalyzed asymmetric hydrosilylation of ketones (up to 94% ee). In particular, the hydrosilylation of 2-octanone yielded (S)-2-octanol with 77% ee.
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U2 - 10.1016/j.tetasy.2004.04.033
DO - 10.1016/j.tetasy.2004.04.033
M3 - Article
AN - SCOPUS:3843120162
SN - 0957-4166
VL - 15
SP - 2263
EP - 2271
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 14
ER -