Reduction of Trifluoromethyl Ketones with Diethyl Zinc Catalyzed by Chiral Monophosphoryl Protected Diamine

doi:10.6023/cjoc202102048

Abstract

In order to obtain trifluoromethylated organic compounds with important biological activity, using phosphoramide as catalyst, diethylzinc and trifluoromethyl aromatic aldehyde as reactants, chiral trifluoromethylated organic compounds were synthesized through catalytic asymmetricβ-H transfer reduction reaction. The raw materials are cheap and easy to obtain, and the catalytic efficiency is high. The yield and ee value can be guaranteed to be highly and simultaneously under the optimized reaction conditions. Despite the large amount of catalyst, the ligand is very convenient to recycle and reuse in this system. At the same time, the reaction mechanism was speculated, and it was considered that the high stereoselectivity of the reaction was due to the formation of two six membered ring transition states and steric hindrance.

Key words: phosphoramide ligand, asymmetric catalysis, chiral trifluoromethylated compound

Cite this article

Xue Wang. Reduction of Trifluoromethyl Ketones with Diethyl Zinc Catalyzed by Chiral Monophosphoryl Protected Diamine[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2693-2699.

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Entry	Ligand	X	R¹	R²	Yield/%	ee^b/%	Config.^c
1	10^[16d]	—	—	—	77	48	R
2	11a^[16c]	O	—	—	20	12	S
3	11b^[16c]	S	—	—	19	11	S
4	9a	O	Bn	Bn	96	55	R
5	9b^[16a]	S	Bn	Bn	93	48	R
6	9c^[16a]	O	Et	H	75	8	R
7	9d^[16a]	O	i-Pr	H	88	19	S

Entry	Ligand	X	R¹	R²	Yield/%	ee^b/%	Config.^c
1	10^[16d]	—	—	—	77	48	R
2	11a^[16c]	O	—	—	20	12	S
3	11b^[16c]	S	—	—	19	11	S
4	9a	O	Bn	Bn	96	55	R
5	9b^[16a]	S	Bn	Bn	93	48	R
6	9c^[16a]	O	Et	H	75	8	R
7	9d^[16a]	O	i-Pr	H	88	19	S

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