Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol

被引：126

作者：

Bertozzi, F

Pineschi, M

Macchia, F

Arnold, LA

Minnaard, AJ

Feringa, BL

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

[2] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol026220u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of ant stereoselectlvity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).

引用

页码：2703 / 2705

页数：3

共 22 条

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Bertozzi F, 2001, ANGEW CHEM INT EDIT, V40, P930, DOI 10.1002/1521-3773(20010302)40:5<930::AID-ANIE930>3.0.CO

[2]

2-7

[3]

Chiu P, 1997, TOP CURR CHEM, V190, P1

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