Applications of Higher-Order Mixed Organocuprates to Organic Synthesis

Bruce H. Lipshutz

doi:10.1055/s-1987-27937

Synthesis 1987; 1987(4): 325-341
DOI: 10.1055/s-1987-27937

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Applications of Higher-Order Mixed Organocuprates to Organic Synthesis

Bruce H. Lipshutz^*

^*Department of Chemistry, University of California, Santa Barbara, CA 93106, U.S.A.

Abstract

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Recent developments in the chemistry of higher-order cyanocuprates are discussed, including the appearance and use of several new reagents prepared from copper(I) cyanide (CuCN) or copper(I) thiocyanate (CuSCN) and two equivalents of various organometallics. Numerous applications to synthetic problems in natural products chemistry are also described. 1. Introduction 2. New Synthetic Methodology 2.1. R₂Cu(CN)Li₂/CO 2.1.1. RCu(CN)Li/CO 2.2. (R₃Si)₂Cu(CN)Li₂ 2.3. R_TR_RCu(CN)Li₂ 2.3.1. Effects of Lewis Acids 2.4. R_TR_RCu(CN)LiM 2.4.1. R_TR_RCu(CN)Li[(n-C₄H₉)₄N] 2.4.2. R_TR_RCu(CN)LiMgX 2.5. R₂Cu(SCN)Li₂ 3. Uses of Higher-Order Cyanocuprates in Synthesis 3.1. Applications to Natural Products Total Synthesis 3.1.1. Epoxide Openings 3.1.2. Other Displacement Reactions 3.1.3. Conjugate Additions 3.1.4. 1,2-Additions 4. Concluding Remarks

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