Theoretically Based Alkylation Reaction Pathways

A similar reaction pathway was found for the Sn2 substitution of an epoxide with a lithium cuprate cluster [124]. In contrast to that in the MeBr reaction, the stereochemistry of the electrophilic carbon center is already inverted in the transition state, providing the reason for the preferred trans-diaxial epoxide-opening widely observed in synthetic studies. The TS for the Sn2 reaction of cyclohexene oxide is shown in Eq. 10.12. 

W Mechanisms of Copper-mediated Addition and Substitution Reactions 

Sdi m 10.11. Reactior betweer R Ciili LiX ard ar allcylatirg agert R Z. Solvert coordirated to lithium atomc ic omitted. 

A similar reaction patliway was found for tlie S u2 substitution of an epoxide witli a litliiuni aiprate duster [ 124]. tn contrast to tliat in tlie MeBr reaction, tlie ste-reodieniistry of tlie dectropb dic carbon center is already inverted in tlie transition state, providing tlie reason for tlie prefetLed rrons-diaxial epoxide-opetiing widely observed in syntlietic studies. Hie TS for tlie S 2 reaction of cydobexene oxide is shown in Eq. 10.12. 

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