Synthesis of modified H4-BINOL ligands and their applications in the asymmetric addition of diethylzinc to aromatic aldehydes

Yong Na Lu; Qun Sheng Guo; Fu Yong Jiang; Jin Shan Li

doi:10.1016/j.tetasy.2006.06.042

Synthesis of modified H₄-BINOL ligands and their applications in the asymmetric addition of diethylzinc to aromatic aldehydes

Yong Na Lu
, Qun Sheng Guo
, Fu Yong Jiang
, Jin Shan Li

Nankai University

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

7 Scopus citations

Abstract

Two new ligands (S,S)-3-(1,1′-bi-2-naphthol-3-yl)-5,6,7,8-tetrahydro-1,1′-bi-2-naphthol [(S,S)-1] and (S)-3-(morpholin-4-ylmethyl)-H₄-BINOL [(S)-2] have been synthesized via Suzuki cross-coupling reaction and a Mannich-type reaction, respectively. In the presence of titanium tetraisopropoxide, 0.8 mol % of ligand (S,S)-1 catalyzed the asymmetric addition of diethylzinc to aromatic aldehydes in good yield and with high enantioselectivity.

Original language	English
Pages (from-to)	1842-1845
Number of pages	4
Journal	Tetrahedron Asymmetry
Volume	17
Issue number	12
DOIs	https://doi.org/10.1016/j.tetasy.2006.06.042
State	Published - 31 Jul 2006
Externally published	Yes

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title = "Synthesis of modified H4-BINOL ligands and their applications in the asymmetric addition of diethylzinc to aromatic aldehydes",

abstract = "Two new ligands (S,S)-3-(1,1′-bi-2-naphthol-3-yl)-5,6,7,8-tetrahydro-1,1′-bi-2-naphthol [(S,S)-1] and (S)-3-(morpholin-4-ylmethyl)-H4-BINOL [(S)-2] have been synthesized via Suzuki cross-coupling reaction and a Mannich-type reaction, respectively. In the presence of titanium tetraisopropoxide, 0.8 mol \% of ligand (S,S)-1 catalyzed the asymmetric addition of diethylzinc to aromatic aldehydes in good yield and with high enantioselectivity.",

author = "Lu, \{Yong Na\} and Guo, \{Qun Sheng\} and Jiang, \{Fu Yong\} and Li, \{Jin Shan\}",

year = "2006",

month = jul,

day = "31",

doi = "10.1016/j.tetasy.2006.06.042",

language = "英语",

volume = "17",

pages = "1842--1845",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

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number = "12",

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T1 - Synthesis of modified H4-BINOL ligands and their applications in the asymmetric addition of diethylzinc to aromatic aldehydes

AU - Lu, Yong Na

AU - Guo, Qun Sheng

AU - Jiang, Fu Yong

AU - Li, Jin Shan

PY - 2006/7/31

Y1 - 2006/7/31

N2 - Two new ligands (S,S)-3-(1,1′-bi-2-naphthol-3-yl)-5,6,7,8-tetrahydro-1,1′-bi-2-naphthol [(S,S)-1] and (S)-3-(morpholin-4-ylmethyl)-H4-BINOL [(S)-2] have been synthesized via Suzuki cross-coupling reaction and a Mannich-type reaction, respectively. In the presence of titanium tetraisopropoxide, 0.8 mol % of ligand (S,S)-1 catalyzed the asymmetric addition of diethylzinc to aromatic aldehydes in good yield and with high enantioselectivity.

AB - Two new ligands (S,S)-3-(1,1′-bi-2-naphthol-3-yl)-5,6,7,8-tetrahydro-1,1′-bi-2-naphthol [(S,S)-1] and (S)-3-(morpholin-4-ylmethyl)-H4-BINOL [(S)-2] have been synthesized via Suzuki cross-coupling reaction and a Mannich-type reaction, respectively. In the presence of titanium tetraisopropoxide, 0.8 mol % of ligand (S,S)-1 catalyzed the asymmetric addition of diethylzinc to aromatic aldehydes in good yield and with high enantioselectivity.

UR - https://www.scopus.com/pages/publications/33746396402

U2 - 10.1016/j.tetasy.2006.06.042

DO - 10.1016/j.tetasy.2006.06.042

M3 - 文章

AN - SCOPUS:33746396402

SN - 0957-4166

VL - 17

SP - 1842

EP - 1845

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 12

ER -

Synthesis of modified H₄-BINOL ligands and their applications in the asymmetric addition of diethylzinc to aromatic aldehydes

Abstract

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