Russian Chemical Bulletin, volume 64, issue 7, pages 1595-1601

Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL

K.N Gavrilov ¹

S V Zheglov ¹

I M Novikov ¹

I V Chuchelkin ¹

V K Gavrilov ¹

V V Lugovsky ¹

I A Zamilatskov ²

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S. A. Esenin Ryazan State University, Ryazan, Russian Federation |

A. N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences, Moscow, Russian Federation |

Publication type: Journal Article

Publication date: 2015-07-01

Springer Nature

Journal: Russian Chemical Bulletin

scimago Q3

SJR: 0.292

CiteScore: 2.7

Impact factor: 1.7

ISSN: 10665285, 15739171

DOI: 10.1007/s11172-015-1047-7

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General Chemistry

Abstract

Novel P*- and P-monodentate phosphoramidites of a 1,3,2-dioxaphosphepine series were derived from (S a)-3-trimethylsilyl-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL. Catalytic performance of the synthesized compounds were examined in the Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate: the reaction with dimethyl malonate gave up to 92% ee. The effects of additives of 5,10,15,20-tetraphenylporphyrin and its metal complexes on conversion and enantioselectivity were studied.

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Current Organic Chemistry	Current Organic Chemistry, 1, 7.69% Current Organic Chemistry 1 publication, 7.69%
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Springer Nature	Springer Nature, 4, 30.77% Springer Nature 4 publications, 30.77%
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Publisher

Springer Nature

Journal

Russian Chemical Bulletin

scimago Q3

SJR

0.292

CiteScore

2.7

Impact factor

1.7

ISSN

10665285 (Print)

15739171 (Electronic)

Labs

Laboratory of Coordination Chemistry

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Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL

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