A HIGHLY DIASTEREOSELECTIVE TANDEM MICHAEL-MICHAEL ADDITION-REACTION IN A ROTAMERIC RING-SYSTEM - STERIC ACCELERATION DUE TO CONFORMATION LOCKING

被引：4

作者：

SAITO, K ^{[1
]}

YAMAMOTO, M ^{[1
]}

YAMADA, K ^{[1
]}

TAKAGI, H ^{[1
]}

机构：

[1] NIPPON SODA CO LTD,ORGAN SYNTH LAB,ODAWARA,KANAGAWA 25002,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(01)80175-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective one-pot tandem Michael-Michael addition reaction developed in a rotamerically locked conformation is described. Reaction of isocyanates 8 - 13 with hydroxylactone 14 gave tandem Michael-Michael adducts 22 - 26 in good to excellent yields. The intermediate tricyclic oxazolidinones consisted of rotamer pairs 16 - 19, and the rotation barriers of some of these compounds were determined. The tandem addition reaction was highly accelerated by introducing conformation anchoring group X. A new versatile synthesis of octahydroacridines 27 - 29 using the tandem adducts is also described.

引用

页码：9721 / 9734

页数：14

共 3 条

[1] A RING EXPANSION PROCEDURE BASED ON THE TANDEM DEALKOXYCARBONYLATION MICHAEL ADDITION-REACTION
BUNCE, RA
SCHILLING, CL
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09): : 2748 - 2752
[2] A RING EXPANSION PROCEDURE BASED ON THE TANDEM DEALKOXYCARBONYLATION-MICHAEL ADDITION-REACTION
BUNCE, RA
SCHILLING, CL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 273 - ORGN
[3] THE TANDEM MICHAEL-S(N)2 REACTION FOR THE CONSTRUCTION OF THE 3-AZABICYCLO[3.1.0]HEXANE RING-SYSTEM
CHAN, S
BRAISH, TF
TETRAHEDRON, 1994, 50 (33) : 9943 - 9950

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