Chelation-Assisted C−O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s) | Zendy

Sue-Min Yeh | Zendy; Gene Hsiang Lee | Zendy; Yu Wang | Zendy; TienYau Luh | Zendy

Open Access

Chelation-Assisted C−O Bond Cleavage of Ortho Esters. A Convenient Synthesis of myo-Inositol Derivatives Having Free Hydroxy Group(s) at Specific Position(s)

Author(s) -

Sue-Min Yeh,

Gene Hsiang Lee,

Yu Wang,

TienYau Luh

Publication year - 1997

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo970606e

Subject(s) - chemistry , chelation , inositol , bond cleavage , stereochemistry , cleavage (geology) , group (periodic table) , medicinal chemistry , organic chemistry , catalysis , biochemistry , receptor , geotechnical engineering , fracture (geology) , engineering

Reactions of ortho esters of myo-inositol 8 or 10 with 1-2 equiv of Grignard reagents in benzene-ether yield regio- and stereoselectively the corresponding ring opening products having a free hydroxy group at C-1. The regioselectivity is rationalized owing to the presence of the 2-methoxy group which will serve as an auxiliary to form a chelation complex 12 with magnesium. Inositol derivatives having two free hydroxy group at C-1 and C-3 positions can be achieved from reactions of 6 or 8 with excess Grignard reagents or under more drastic conditions. The reaction of 8b with excess LiAlH(4)/AlCl(3), on the other hand, yields the corresponding 1,5-diol 19.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research