TY - JOUR
T1 - Direct synthesis of substituted tetrahydrofurans via regioselective dehydrative polyol cyclization cascades
AU - Dounay, Amy B.
AU - Florence, Gordon John
AU - Saito, Akira
AU - Forsyth, Craig J.
PY - 2002/3/4
Y1 - 2002/3/4
N2 - A one-pot procedure for the conversion of 1,2,4,5-tetraols into substituted tetrahydrofuran moieties has been developed. This involves the regioselective sulfonylation of the terminal hydroxyl of the polyol array followed by sequential oxirane and oxolane formation under basic conditions. A survey of reaction conditions has defined the use of N-(2,4,6-triisopropylbenzenesulfonyl)imidazole as sulfonylation reagent, potassium tert-butoxide as base, and tert-butanol as solvent to be optimal. Under these conditions, 8-O-benzyl-octan-1,2,4,5,8-pentaol was converted stereospecifically into tetrahydrofurans in 62% yield. Polyol substrates were derived from Sharpless asymmetric dihydroxylation of 1,4-dienes. Hence, substituted tetrahydrofurans could be obtained stereospecifically from diene substrates in two operations. (C) 2002 Elsevier Science Ltd. All rights reserved.
AB - A one-pot procedure for the conversion of 1,2,4,5-tetraols into substituted tetrahydrofuran moieties has been developed. This involves the regioselective sulfonylation of the terminal hydroxyl of the polyol array followed by sequential oxirane and oxolane formation under basic conditions. A survey of reaction conditions has defined the use of N-(2,4,6-triisopropylbenzenesulfonyl)imidazole as sulfonylation reagent, potassium tert-butoxide as base, and tert-butanol as solvent to be optimal. Under these conditions, 8-O-benzyl-octan-1,2,4,5,8-pentaol was converted stereospecifically into tetrahydrofurans in 62% yield. Polyol substrates were derived from Sharpless asymmetric dihydroxylation of 1,4-dienes. Hence, substituted tetrahydrofurans could be obtained stereospecifically from diene substrates in two operations. (C) 2002 Elsevier Science Ltd. All rights reserved.
KW - tetrahydrofurans
KW - cyclization
KW - 1,4-dienes
KW - ENOLATE CLAISEN REARRANGEMENT
KW - ASYMMETRIC DIHYDROXYLATION
KW - STEREOCHEMICAL CONTROL
KW - NATURAL-PRODUCTS
KW - LIGAND CLASS
KW - OLEFINS
UR - http://www.scopus.com/inward/record.url?scp=0037017721&partnerID=8YFLogxK
UR - http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THR-455TTV9-4&_coverDate=03%2F04%2F2002&_alid=444818467&_rdoc=1&_fmt=&_orig=search&_qd=1&_cdi=5289&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=6ddcb8217adb549d713cc9f0b25ca32c
U2 - 10.1016/S0040-4020(02)00043-1
DO - 10.1016/S0040-4020(02)00043-1
M3 - Article
SN - 0040-4020
VL - 58
SP - 1865
EP - 1874
JO - Tetrahedron
JF - Tetrahedron
IS - 10
ER -