1,1'-(AZODICARBONYL)DIPIPERIDINE-TRIBUTYLPHOSPHINE, A NEW REAGENT SYSTEM FOR MITSUNOBU REACTION

被引：251

作者：

TSUNODA, T

YAMAMIYA, Y

ITO, S

机构：

[1] Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 10期

关键词：

D O I：

10.1016/0040-4039(93)85029-V

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,1'-(azodicarbonyl)dipiperidine (ADDP)-tributylphosphine (TBP) system was developed as a new substitute of the Mitsunobu reagent. The new system activates nitrogen or carbon nucleophiles, known to be innert or poorly reactive with the Mitsunobu reagent, to react with alcohols satisfactorily forming C-N or C-C bonds. The inversion of stereogenic carbinyl carbons was confirmed in the acylaltion reaction of two sec-alcohols.

引用

页码：1639 / 1642

页数：4

共 10 条

[1] BOSE AK, 1973, TETRAHEDRON LETT, P1619
[2] SOME OBSERVATIONS ON THE MECHANISM OF THE MITSUNOBU REACTION
CRICH, D
DYKER, H
HARRIS, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (01) : 257 - 259
[3] STEREOSPECIFIC SYNTHESIS OF SECONDARY-AMINES BY THE MITSUNOBU REACTION
EDWARDS, ML
STEMERICK, DM
MCCARTHY, JR
[J]. TETRAHEDRON LETTERS, 1990, 31 (24) : 3417 - 3420
[4] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES
HENRY, JR
MARCIN, LR
MCINTOSH, MC
SCOLA, PM
HARRIS, GD
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1989, 30 (42) : 5709 - 5712
[5] A MECHANISTIC STUDY OF THE MITSUNOBU ESTERIFICATION REACTION
HUGHES, DL
REAMER, RA
BERGAN, JJ
GRABOWSKI, EJJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) : 6487 - 6491
[6] PREPARATION OF CARBOXYLIC ESTERS AND PHOSPHORIC ESTERS BY ACTIVATION OF ALCOHOLS
MITSUNOBU, O
EGUCHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (12) : 3427 - +
[7] THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS
MITSUNOBU, O
[J]. SYNTHESIS-STUTTGART, 1981, (01): : 1 - 28
[8] MECHANISTIC IMPLICATIONS OF 1,3,2-LAMBDA-5-DIOXAPHOSPHOLANES IN THE MITSUNOBU REACTION
PAUTARDCOOPER, A
EVANS, SA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) : 2485 - 2488
[9] A REVISED MECHANISM FOR THE MITSUNOBU REACTION
VARASI, M
WALKER, KAM
MADDOX, ML
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) : 4235 - 4238
[10] WADA M, 1972, TETRAHEDRON LETT, P1279

← 1 →