SE‘ Reactions

Sophisticated methodologies for SE‘ reactions to afford stereocontrolled preparation of homoallylic alcohols have been studied for making highly functionalized systems to support applications to natural product chemisty. A brief outline of these efforts:

A) Bidirectional SE‘ strategies for 1,5-stereocontrol

meth6A

Primary reference: Org. Lett. 2012, 14, 3866-3869.

B) Stereocontrol in Asymmetric SE‘ reactions of gamma-substituted α,β-unstaurated aldehydes

meth6B

Primary reference: Org. Lett. 2014, 16, 468-471.

C) Bis-Stannylation of 1-Alkoxyallene and stereocontrolled allylation

meth6C

Primary reference: J. Am. Chem. Soc. 2005, 127, 14550-14551.

D) Allylation SE‘ Reactivity of 3,3-Bis(trimethylsily)-2-methyl-1-propene.

meth6D

Primary reference: Org. Lett. 2006, 8, 4393-4396.

E) The role of vicinal chirality in SE' reactions

meth6E

Primary reference: Can. J. Chem. 2004, 82, 120-130.

F) Asymmetric SE’ reactions in the Total Synthesis of Phorboxazole A.

meth6F

Primary reference: Proc. Natl. Acad. Sci. (USA) 2004, 101, 12058-12063.

G) Asymmertric SE’ reactions for the synthesis of Amphidinolide K.

meth6G

Primary reference: J. Am. Chem. Soc. 2001, 123, 765-767.

H) Asymmertric SE’ reactions; an application for total synthesis of (−)-Laulimalide

meth6H

Primary reference: Tet. Lett. 2002, 43, 4841-4844.

I) Asymmetric SE’ methodology for Total Synthesis of Leucascandrolide A.

meth6I

Primary reference: Angew. Chem. Int. Ed. 2003, 42, 3934-3938.

J) Stereoconvergent SE’ reactions of chiral allylsilanes in the synthesis of Deoxyneodolabelline

meth6J

Primary reference: J. Am. Chem. Soc. 2003, 125, 1843-1850.

K) Reagent-Controlled asymmertric allylation in the synthesis of Hennoxazole A.

meth6K

Primary reference: J. Am. Chem. Soc. 1999, 121, 4924-4925.