INVERSION OF CONFIGURATION OF ALPHA-TRISUBSTITUTED (NEOPENTYL) TYPE SECONDARY ALCOHOLS

被引:38
作者
MORIARTY, RM [1 ]
ZHUANG, H [1 ]
PENMASTA, R [1 ]
LIU, K [1 ]
AWASTHI, AK [1 ]
TULADHAR, SM [1 ]
RAO, MSC [1 ]
SINGH, VK [1 ]
机构
[1] INDIAN INST TECHNOL, DEPT CHEM, KANPUR 208016, UTTAR PRADESH, INDIA
关键词
D O I
10.1016/S0040-4039(00)61442-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of hindered alpha-trisubstituted optically active secondary alcohols has been converted into their enantiomers by treating the corresponding triflates with KNO2 in DMF in the presence of 18-crown-6 at room temperature.
引用
收藏
页码:8029 / 8032
页数:4
相关论文
共 22 条
[1]   SYNTHESIS OF THE 12-HYDROXY GIBBERELLINS GA31, GA69 AND GA70 [J].
CHU, A ;
MANDER, LN .
TETRAHEDRON LETTERS, 1988, 29 (22) :2727-2730
[2]  
COREY EJ, 1975, TETRAHEDRON LETT, P3183
[3]   SOME OBSERVATIONS ON THE MECHANISM OF THE MITSUNOBU REACTION [J].
CRICH, D ;
DYKER, H ;
HARRIS, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) :257-259
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]  
DODGE JA, 1993, 205TH ACS NAT M DENV
[6]   MECHANISM OF SUBSTITUTION AT A SATURATED CARBON ATOM .29. THE ROLE OF STERIC HINDRANCE - (SECTION-D) THE MECHANISM OF THE REACTION OF NEOPENTYL BROMIDE WITH AQUEOUS ETHYL ALCOHOL [J].
DOSTROVSKY, I ;
HUGHES, ED .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (MAR) :166-169
[7]   MECHANISM OF SUBSTITUTION AT A SATURATED CARBON ATOM .27. THE ROLE OF STERIC HINDRANCE - (SECTION-B) A COMPARISON OF THE RATES OF REACTION OF ETHYL AND NEOPENTYL BROMIDES WITH INORGANIC IODIDES IN ACETONE SOLUTION [J].
DOSTROVSKY, I ;
HUGHES, ED .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (MAR) :161-164
[8]   MECHANISM OF SUBSTITUTION AT A SATURATED CARBON ATOM .26. THE ROLE OF STERIC HINDRANCE - (SECTION-A) INTRODUCTORY REMARKS, AND A KINETIC STUDY OF THE REACTIONS OF METHYL, ETHYL, N-PROPYL, ISOBUTYL, AND NEOPENTYL BROMIDES WITH SODIUM ETHOXIDE IN DRY ETHYL ALCOHOL [J].
DOSTROVSKY, I ;
HUGHES, ED .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (MAR) :157-161
[9]   MECHANISM OF SUBSTITUTION AT A SATURATED CARBON ATOM .31. THE ROLE OF STERIC HINDRANCE - (SECTION-F) A COMPARISON OF THE RATES OF REACTION OF METHYL, ETHYL, N-PROPYL, AND NEOPENTYL BROMIDES WITH WET FORMIC ACID [J].
DOSTROVSKY, I ;
HUGHES, ED .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (MAR) :171-173
[10]   MECHANISM OF SUBSTITUTION AT A SATURATED CARBON ATOM .30. THE ROLE OF STERIC HINDRANCE - (SECTION-E) A COMPARISON OF THE RATES OF REACTION OF METHYL, ETHYL, N-PROPYL, ISOBUTYL, AND NEOPENTYL HALIDES WITH SILVER NITRATE IN AQUEOUS ETHYL ALCOHOL [J].
DOSTROVSKY, I ;
HUGHES, ED .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (MAR) :169-171