SYNTHESIS OF (R)-2,3-DIHYDRO-2,5-DIMETHYL-2-ISOPROPYLFURAN

被引：11

作者：

BAI, X ^{[1
]}

ELIEL, EL ^{[1
]}

机构：

[1] UNIV N CAROLINA,DEPT CHEM,WR KENAN JR LABS,CHAPEL HILL,NC 27599

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (R)-2,3-dihydro-2,5-dimethyl-2-isopropylfuran (1), an insect pheromone, via a 1,3-oxathiane is reported. Key steps are the preparation of (S)-2,3-dimethylbutane-1,2-diol (7) from isobutyryloxathiane 5 and reaction of lithiated acetone dimethylhydrazone with tosylated diol 8. NMR spectra of the key tautomeric precursors, 2/2'/3, to 1 have been analyzed in detail, and the enantiomeric excess of these precursors was determined by a chiral shift C-13 NMR experiment.

引用

页码：2086 / 2089

页数：4

共 15 条

[1]

COREY EJ, 1976, TETRAHEDRON LETT, P3667

[2] DISTORTIONLESS ENHANCEMENT OF NMR SIGNALS BY POLARIZATION TRANSFER [J].

DODDRELL, DM ;

PEGG, DT ;

BENDALL, MR .

JOURNAL OF MAGNETIC RESONANCE, 1982, 48 (02) :323-327

[3]

DOLGII IE, 1969, IAN SSSR KH, P2275

[4] THE CONFIGURATIONS OF (-)-2,3,3-TRIMETHYL-2-HYDROXYBUTANOIC ACID, ME3CC(ME)(OH)CO2H,(-)-3,4,4-TRIMETHYL-3-HYDROXY-1-PENTYNE AND (-)-3-T-BUTYL-3-METHYL-1-CHLOROALLENE [J].

ELIEL, EL ;

LYNCH, JE .

TETRAHEDRON LETTERS, 1987, 28 (41) :4813-4816

[5] AN IMPROVED SYNTHESIS OF 2-OXATHIANYL KETONES [J].

ELIEL, EL ;

BAI, X ;

ABDELMAGID, AF ;

HUTCHINS, RO .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4951-4953

[6]

ELIEL EL, 1987, ORG SYNTH, V65, P215

[7]

ELIEL EL, 1985, PHOSPHOROUS SULFUR, V24, P73

[8]

FRANCKE W, 1982, C INRA, V7, P85

[9] THE REARRANGEMENT OF ALPHA-BETA-UNSATURATED ALCOHOLS TO SATURATED ALDEHYDES AND KETONES .1. THE PREPARATION OF ALPHA-BETA-UNSATURATED ALCOHOLS AND 1-2-DIOLS AND THEIR PROTOTROPIC CHANGE [J].

GREEN, MB ;

HICKINBOTTOM, WJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUL) :3262-3270

[10] ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .2. SYNTHESIS OF CHIRAL TERTIARY ALPHA-HYDROXY ALDEHYDES, ALPHA-HYDROXY ACIDS, GLYCOLS (RR'C(OH)CH2OH), AND CARBINOLS (RR'C(OH)CH3) IN HIGH ENANTIOMERIC PURITY [J].

LYNCH, JE ;

ELIEL, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) :2943-2948

← 1 2 →