Synthesis of Open‐Chain 2,3‐Disubstituted 4‐nitroketones by Diastereoselective Michael‐addition of (E)‐Enamines to (E)‐Nitroolefins. A topological rule for C, C‐bond forming processes between prochiral centres. Preliminary communication

Helvetica Chimica Acta - Tập 64 Số 5 - Trang 1413-1423 - 1981
Dieter Seebàch1, J. GOLINSKI1,2,3,4
1Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstrasse 16, 8092 Zürich (Switzerland)
2Postdoctoral Research Associate
3We thank Dr. J.N. Hay (Postdoctoral Fellow under the NATO Science Fellowship Scheme, 1979/80) for carrying out some preliminary experiments.
4on leave from the Polish Academy of Sciences, Warsaw (February-April 1981).

Tóm tắt

Abstract

The Michael‐additions of aliphatic, alicyclic, and arylsubstituted nitroolefins and enamines lead to γ‐nitroketones 3 in good chemical and excellent (> 90%) diastereomeric yields (see Table 1).

The known threo‐configuration of one type of adducts 3 (entries 8, 10, and 11 of Table 1) can be arrived at by assuming the approach 8 of the Michael‐acceptor and ‐donor; the reaction follows a topological rule, which is formulated and which is applicable to such diverse reactions as the diene synthesis, cyclopropanations, carbonyl olefinations and methylenations, aldol‐ and nitroaldol‐type additions, as well as additions of lithium, boron, and chromium derivatives to aldehydes (see 9, 10, 11, and Table 2).

Từ khóa


Tài liệu tham khảo

Bartlett P. A., 1981, Tetrahedron, 36, 3

10.1021/ja00495a064

10.1021/ja00495a065

10.1021/ja00495a066

10.1021/ja00526a073

10.1021/ja00396a050

10.1021/ja00396a051

Seebach D., 1979, Chimia, 33, 1

10.1002/ange.19810930433

10.1002/anie.198103971

10.1016/0040-4020(78)88328-8

10.1021/jo01294a030

10.1021/jo00320a014

D. E.Van Horn &S.Masamune Tetrahedron Lett.1979 2229.

10.1021/ja00514a045

10.1021/ja00520a020

10.1021/ja01565a041

10.1002/hlca.19800630727

10.1021/ja00530a052

Houben‐Weyl, 1971, Methoden der Organischen Chemie

Cook A. G., 1969, Enamines

Dyke S. F., 1973, The Chemistry of Enamines

(b)J.Sauer &H.Prahl Tetrahedron Lett.1966 2863.

Ahlbrecht H., 1977, Chimia, 31, 391

10.3891/acta.chem.scand.32b-0335

10.1016/S0040-4020(01)82495-9

10.1016/S0040-4020(01)93436-2

10.1016/S0040-4020(01)97438-1

10.1016/0040-4020(75)87087-6

(e)S.Fabrissin S.Fatutta N.Malusà &A.Risaliti J. Chem. Soc. Perkin I1980 686.

(f)S.Fabrissin S.Fatutta &A.Risaliti Tetrahedron1981 109.

10.1002/cber.19751080615

10.1021/jo01282a046

E. J.Corey &H.Estreicher Tetrahedron Lett.1980 1113.

Seebach D., 1971, Methoden der Organischen Chemie, IV/4

10.1021/jo01023a066

10.1002/ange.19730850602

10.1002/anie.197302121

10.1002/hlca.19720550640

10.1021/ja00431a074

Seebach D., 1979, Helv. Chim. Acta, 62, 2295

10.1021/jo00429a047

10.1002/hlca.19720550736

10.1002/hlca.19800630118

Eliel E. L., 1962, Stereochemistry of Carbon Compounds

10.1515/znb-1965-0501

10.1021/ja00783a077

10.1021/ja00399a063

10.1002/ange.19750871302

10.1002/anie.197504601

10.1351/pac198052040771

Anh N. T., 1977, Nouv. J. Chim., 1, 61

10.1021/ja00798a066

10.1021/ja00400a055

10.1002/ange.19690812102

Woodward R. B., 1969, Int. Ed., 8, 781, 10.1002/anie.196907811

10.1002/ange.19670790203

10.1002/anie.196700161

10.1002/9780470147146.ch1

M.Schlosser Bull. Soc. Chim. Fr.1971 453.

10.1016/0040-4020(77)80265-2

10.1021/ja00529a062

10.1021/ja00398a047

D. A.Evans &L. R.McGee Tetrahedron Lett.1980 3975.

Y.Yamamoto &K.Maruyama Tetrahedron Lett.1980 4607.

Y.Yamamoto H.Yatagai &K.Maruyama J. Chem. Soc. Chem. Commun.1981 162.

E.Fujita M.Shibuya S.Nakamura Y.Okada &T.Fujita J. Chem. Soc. Perkin I 1974 165.

10.1021/jo00925a002

R. A.Appleton K. H.Baggaley S. C.Egan J. M.Davies S. H.Graham &D. O.Lewis J. Chem. Soc. (C)1968 2032 and references cited therein.

K.Wiesner A.Deljac T. Y. R.Tsai &M.Przybylska Tetrahedron Lett.1970 1145.

10.1016/0040-4020(80)80024-X

10.1021/ja00397a058

t.Clark &P. v. R.Schleyer J. Chem. Soc. Chem. Commun.1979 883.

10.1002/hlca.19800630732

Trost B. M., 1975, Sulfur Ylides

Block E., 1977, Reactions of Organosulfur Compounds

10.1021/ja00395a078

10.1002/hlca.19700530223

10.1002/hlca.19810640314

E. W.Colvin &D.Seebach J. Chem. Soc. Chem. Commun.1978 689.

10.1002/hlca.19800630320

10.1002/ange.19800920728

10.1002/anie.198005571

10.1021/ja00517a056

10.1021/ja00398a058

10.1021/ja00401a031

10.1002/ange.19790910413

10.1002/anie.197903061

10.1021/jo00320a015

10.1002/ange.19800920331

10.1002/anie.198002181

R. W.Hoffmann &B.Kemper Tetrahedron Lett.1980 4883.

C. T.Buse &C. H.Heathcock Tetrahedron Lett.1978 1685.

10.5059/yukigoseikyokaishi.39.81

10.1002/cber.19771100630

Thông tin
Thông tin xuất bản

Helvetica Chimica Acta

Tập 64 Số 5

1413-1423

Thông tin tác giả