Chiral N-phosphoryl imines: Design, synthesis and direct asymmetric addition reactions with diketones and diesters

Hao Sun; Trideep Rajale; Yi Pan; Guigen Li

doi:10.1016/j.tetlet.2010.06.072

Chiral N-phosphoryl imines: Design, synthesis and direct asymmetric addition reactions with diketones and diesters

Hao Sun, Trideep Rajale, Yi Pan, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62% - quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.

Original language	English
Pages (from-to)	4403-4407
Number of pages	5
Journal	Tetrahedron Letters
Volume	51
Issue number	33
DOIs	https://doi.org/10.1016/j.tetlet.2010.06.072
State	Published - Aug 18 2010

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abstract = "Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62% - quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.",

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AU - Rajale, Trideep

AU - Pan, Yi

AU - Li, Guigen

PY - 2010/8/18

Y1 - 2010/8/18

N2 - Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62% - quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.

AB - Chiral N-phosphoryl imines derived from (S)-BINOL have been designed and synthesized in good to excellent chemical yields. These N-phosphoryl imines were found to react with diketones smoothly without the use of any bases. They can also serve as electrophiles for the reaction with diethyl malonate in the presence of potassium carbonate. Good yields (62% - quant) and excellent diastereoselectivities (up to 99:1 dr) have been achieved for 10 examples.

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