Deprotonative metalation using ate compounds: Synergy, synthesis, and structure building

被引:477
作者
Mulvey, Robert E.
Mongin, Florence
Uchiyama, Masanobu
Kondo, Yoshinori
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1XL, Lanark, Scotland
[2] Univ Rennes 1, UMR CNRS 6510, F-35042 Rennes, France
[3] RIKEN, Inst Phys & Chem Res, Wako, Saitama 3510198, Japan
[4] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9808578, Japan
关键词
ate complexes; dimetallic complexes; inverse crown compounds; metalation; synthetic methods; DIRECTED ORTHO-METALATION; MAGNESIUM EXCHANGE-REACTION; CATALYZED ASYMMETRIC CARBOALUMINATION; INVERSE CROWN CHEMISTRY; 14-MEMBERED DIENE UNIT; ALLENIC ZINC REAGENTS; DIANION-TYPE ZINCATE; MEDIATED ZINCATION; CRYSTAL-STRUCTURE; ALKENYLMAGNESIUM REAGENTS;
D O I
10.1002/anie.200604369
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Historically, single-metal organometallic species such as organolithium compounds have been the reagents of choice in synthetic organic chemistry for performing deprotonation reactions. Over the past few years, a complementary new class of metalating agents has started to emerge. Owing to a variable central metal (magnesium, zinc, or aluminum), variable ligands (both in their nature and number), and a variable second metallic center (an alkali metal such as lithium or sodium), "ate" complexes are highly versatile bases that exhibit a synergic chemistry which cannot be replicated by the homometallic magnesium, zinc, or aluminum compounds on their own. Deprotonation accomplished by using these organometallic ate complexes has opened up new perspectives in organic chemistry with unprecedented reactivities and sometimes unusual and unpredictable regioselectivities. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3802 / 3824
页数:23
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