A novel reaction of α-haloepoxides with trialkylstannates

LD Corey, SM Singh…

Index: Corey, L. D.; Singh, S. M.; Oehlschlager, A. C. Canadian Journal of Chemistry, 1987 , vol. 65, p. 1821 - 1827

Full Text: HTML

Citation Number: 14

Abstract

The reaction of α-haloepoxides with zinc powder or reagents containing the trialkylstannate anion yields allylic alcohols by anti elimination of the carbon halogen and adjacent carbon epoxy oxygen bonds. Appreciable Z→ E isomerization occurs in both types of reactions but the experimental results indicate that the conversion of erythro α-bromoepoxides to E allylic alcohols by zinc or trialkylstannates shows sufficient stereospecificity to be synthetically ...

Related Articles:

A novel one-pot synthesis of secondary alcohols from esters

[Chae, Min Jung; Jeon, Ah Ram; Park, Jae Kyo; An, Duk Keun Tetrahedron Letters, 2011 , vol. 52, # 14 p. 1718 - 1720]

The semihydrogenation of acetylenes over Pd catalyst on BER in the presence of CsI

[Yoon, Nung Min; Park, Kyung Bae; Lee, Hyun Ju; Choi, Jaesung Tetrahedron Letters, 1996 , vol. 37, # 47 p. 8527 - 8528]

Chemoenzymatic Asymmetric Total Synthesis of Nonanolide (Z)??Cytospolides D, E and Their Stereoisomers

[Rej, Rohan Kalyan; Nanda, Samik European Journal of Organic Chemistry, 2014 , vol. 2014, # 4 p. 860 - 871]

Efficient tetrahydropyranylation of alcohols and detetrahydropyranylation reactions in the presence of catalytic amount of trichloroisocyanuric acid (TCCA) as a safe, …

[Firouzabadi, Habib; Iranpoor, Nasser; Hazarkhani, Hassan Synthetic Communications, 2004 , vol. 34, # 19 p. 3623 - 3630]

l-Proline-derived ligands to mimic the '2-His-1-carboxylate'triad of the non-haem iron oxidase active site

[Dungan, Victoria J.; Wong, Shwo Mun; Barry, Sarah M.; Rutledge, Peter J. Tetrahedron, 2012 , vol. 68, # 15 p. 3231 - 3236]

More Articles...