Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/Z-Isomerization, Regioselectivity, and Synthetic Applications

2019 ◽  
Vol 84 (18) ◽  
pp. 11458-11473 ◽  
Author(s):  
Masaharu Sugiura ◽  
Yasuhiko Ashikari ◽  
Yuka Takahashi ◽  
Koki Yamaguchi ◽  
Shunsuke Kotani ◽  
...  
Keyword(s):  
Lewis Base ◽  
Unsaturated Ketones ◽  
Conjugate Reduction

Asymmetric Conjugate Reduction of α,β-Unsaturated Ketones and Esters with Chiral Rhodium(2,6-bisoxazolinylphenyl) Catalysts.

ChemInform ◽  
2006 ◽  
Vol 37 (19) ◽  
Author(s):  
Yoshinori Kanazawa ◽  
Yasunori Tsuchiya ◽  
Kazuki Kobayashi ◽  
Takushi Shiomi ◽  
Jun-ichi Itoh ◽  
...  
Keyword(s):  
Unsaturated Ketones ◽  
Conjugate Reduction

A Tertiary Amine as A Hydride Donor: Trichlorosilyl Triflate-mediated Conjugate Reduction of Unsaturated Ketones

2011 ◽  
Vol 13 (15) ◽  
pp. 3968-3971 ◽  
Author(s):  
Shunsuke Kotani ◽  
Kazuki Osakama ◽  
Masaharu Sugiura ◽  
Makoto Nakajima
Keyword(s):  
Tertiary Amine ◽  
Unsaturated Ketones ◽  
Conjugate Reduction

scholarly journals Conjugate Reduction of α,β-Unsaturated Ketones with Amphiphilic Reaction System

1988 ◽  
Vol 61 (6) ◽  
pp. 2241-2243 ◽  
Author(s):  
Katsumasa Nonoshita ◽  
Keiji Maruoka ◽  
Hisashi Yamamoto
Keyword(s):  
Reaction System ◽  
Unsaturated Ketones ◽  
Conjugate Reduction

Organotin Hydride-Catalyzed Conjugate Reduction of α,β-Unsaturated Ketones

1996 ◽  
Vol 61 (19) ◽  
pp. 6751-6752 ◽  
Author(s):  
David S. Hays ◽  
Matthias Scholl ◽  
Gregory C. Fu
Keyword(s):  
Unsaturated Ketones ◽  
Conjugate Reduction

Triphenylphosphine Oxide-Catalyzed Selective α,β-Reduction of Conjugated Polyunsaturated Ketones

Synlett ◽  
2019 ◽  
Vol 30 (09) ◽  
pp. 1100-1104 ◽  
Author(s):  
Xuanshu Xia ◽  
Zhiqi Lao ◽  
Patrick Toy
Keyword(s):  
Wittig Reaction ◽  
Building Blocks ◽  
Triphenylphosphine Oxide ◽  
Reduction Reaction ◽  
Natural Product Synthesis ◽  
Reaction Sequence ◽  
One Pot ◽  
Unsaturated Ketones ◽  
Naturally Occurring ◽  
Conjugate Reduction

The scope of the triphenylphosphine oxide-catalyzed reduction of conjugated polyunsaturated ketones using trichlorosilane as the reducing reagent has been examined. In all cases studied, the α,β-C=C double bond was selectively reduced to a C–C single bond while all other reducible functional groups remained unchanged. This reaction was applied to a large variety of conjugated dienones, a trienone, and a tetraenone. Additionally, a tandem one-pot Wittig/conjugate-reduction reaction sequence was developed to produce γ,δ-unsaturated ketones directly from simple building blocks. In these reactions the byproduct of the Wittig reaction served as the catalyst for the reduction reaction. This strategy was then used in the synthesis of naturally occurring moth pheromones to demonstrate its utility in the context of natural-product synthesis.

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