Process for preparing higher order cuprate complexes

Details Process for preparing higher order cuprate complexes Process for preparing higher order cuprate complexes

1987-06-08

1988-11-15

Shaver, Paul F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

556 87, 556112, C07F 108, C07F 722

Patent

active

047851244

ABSTRACT:
This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as epoxide addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes derived from the reaction of a cuprate complex with 1,2-bis-tri-n-butylstannyl ethylene are particularly useful for the addition to epoxides to form vinyl tin intermediates useful for preparing omega side chains of prostaglandins.

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Lipshutz "Applications of Higher Order Mixes Organocuprates to Organic Synthesis:," Synthesis, 4, p. 325 (1987).
Bindra and Bindra, "Prostaglandin Synthesis", Academic Press, Inc. N.Y. Chapter 7, pp. 99-108.
Collins, J. Med. Chem., 29, 437 (1986).
Corey, et al., J.A.C.S., 94, 7210-11 (1972).

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