Abstract
Grignard reagents, especially isopropylmagnesium chloride, smoothly undergo Michael addition onto methyl 2-bromo- and 2-chloro-2-cyclopropylideneacetate (1 -Cl), and the thus formed magnesium enolates are particularly efficiently trapped with aromatic aldehydes. This one-pot reaction provides highly substituted chlorohydrines, mostly in high yields (10 out of 18 examples with 72-92%) and as pure (2S *,3R *)-diastereomers (anti -aldols). These chlorohydrines can be transformed to Darzens-type α,β-epoxyesters in good yields, as demonstrated for one example.
Key words
small ring systems - Michael additions - aldol reactions - domino reactions - diastereoselectivity - synthetic methods
References
1a Part 119 in the series ‘Cyclopropyl Building Blocks for Organic Synthesis’.
1b For part 118 see: Yucel, B.; Arve, L.; de Meijere, A. Tetrahedron 2005 , 61, 11355.
1c Part 117: Bräse, A.; Nüske, H.; Frank, D.; de Meijere, A. Eur. J. Org. Chem. 2005 , 4167.
2a Liese T.
Splettstösser G.
de Meijere A.
Angew. Chem., Int. Ed. Engl.
1982,
21:
790 ; Angew. Chem. 1982 , 94 , 799
2b Liese T.
Seyed-Mahdavi F.
de Meijere A.
Org. Synth.
1990,
69:
148
2c 1 -Br and 1 -Cl see: Limbach M.
Dalai S.
de Meijere A.
Adv. Synth. Catal.
2004,
346:
760
3a de Meijere A.
Bull. Soc. Chim. Belg.
1984,
93:
241
3b de Meijere A.
Wessjohann L.
Synlett
1990,
20
3c de Meijere A. In
New Aspects of Organic Chemistry II , Proceedings of the Fifth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC 5, Kyoto, Nov. 11-15, 1991)
Oshiro Y.
Kodansha;
Tokyo:
1992.
p.181
3d de Meijere A.
Kozhushkov SI.
Hadjiarapoglou L.
Top. Curr. Chem.
1999,
207:
149
4a Brandi A.
Cicchi S.
Cordero FM.
Goti A.
Chem. Rev.
2003,
103:
1213
4b Nakamura I.
Yamamoto Y.
Adv. Synth. Catal.
2002,
344:
111
5a Liese T.
Teichmann S.
de Meijere A.
Synthesis
1988,
25
5b Seyed-Mahdavi F.
Teichmann S.
de Meijere A.
Tetrahedron Lett.
1986,
27:
6185
6a Spitzner D.
Engler A.
Liese T.
Splettstößer G.
de Meijere A.
Angew. Chem., Int. Ed. Engl.
1982,
21:
791 ; Angew. Chem. 1982 , 94 , 799
6b Spitzner D.
Engler A.
Wagner P.
de Meijere A.
Bengtson G.
Simon A.
Peters K.
Peters E.-M.
Tetrahedron
1987,
43:
3213
6c Hadjiarapoglou L.
Klein I.
Spitzner D.
de Meijere A.
Synthesis
1996,
525
6d de Meijere A.
Teichmann S.
Seyed-Mahdavi F.
Kohlstruk S.
Liebigs Ann.
1996,
1989
6e Wessjohann L.
Giller K.
Zuck B.
Skattebøl L.
de Meijere A.
J. Org. Chem.
1993,
58:
6442
6f Hadjiarapoglou L.
de Meijere A.
Seitz H.-J.
Klein I.
Spitzner D.
Tetrahedron Lett.
1994,
35:
3269
6g de Meijere A.
Hadjiarapoglou LP.
Noltemeyer M.
Gutke H.-J.
Klein I.
Spitzner D.
Eur. J. Org. Chem.
1998,
441
7a de Meijere A.
Teichmann S.
Yu D.
Kopf J.
Oly M.
von Thienen N.
Tetrahedron
1989,
45:
2957
7b Wessjohann L.
Skattebøl L.
de Meijere A.
J. Chem. Soc., Chem. Commun.
1990,
574
7c Giller K.
Baird MS.
de Meijere A.
Synlett
1992,
524
7d Es-Sayed M.
Heiner T.
de Meijere A.
Synlett
1993,
57
7e Zorn C.
Goti A.
Brandi A.
Johnsen K.
Kozhushkov SI.
de Meijere A.
Chem. Commun.
1998,
903
7f Nötzel MW.
Tamm M.
Labahn T.
Noltemeyer M.
Es-Sayed M.
de Meijere A.
J. Org. Chem.
2000,
65:
3850
7g Nötzel MW.
Labahn T.
Es-Sayed M.
de Meijere A.
Eur. J. Org. Chem.
2001,
3025
7h Nötzel MW.
Rauch K.
Labahn T.
de Meijere A.
Org. Lett.
2002,
4:
839
7i Zorn C.
Goti A.
Brandi A.
Johnsen K.
Noltemeyer M.
Kozhushkov SI.
de Meijere A.
J. Org. Chem.
1999,
64:
755
8a Wessjohann L.
McGaffin G.
de Meijere A.
Synthesis
1989,
359
8b Wessjohann L.
Krass N.
Yu D.
de Meijere A.
Chem. Ber.
1992,
125:
867
8c Es-Sayed M.
Gratkowski C.
Krass N.
Meyers AI.
de Meijere A.
Synlett
1992,
962
8d Es-Sayed M.
G ratkowski C.
Krass N.
Meyers AI.
de Meijere A.
Tetrahedron Lett.
1993,
34:
289
8e Tamm M.
Thutewohl M.
Ricker CB.
Bes MT.
de Meijere A.
Eur. J. Org. Chem.
1999,
2017
9a Belov VN.
Funke C.
Labahn T.
Es-Sayed M.
de Meijere A.
Eur. J. Org. Chem.
1999,
1345
9b Funke C.
Es-Sayed M.
de Meijere A.
Org. Lett.
2000,
2:
4249
9c Limbach M.
Dalai S.
Janssen A.
Es-Sayed M.
Magull J.
de Meijere A.
Eur. J. Org. Chem.
2005,
610
10a Gawley RE.
Synthesis
1976,
777
10b Notz W.
Tanaka F.
Barbas CF.
Acc. Chem. Res.
2004,
37:
580
11a Posner GH.
Chem. Rev.
1986,
86:
831
11b Tietze LF.
Beifuss U.
Angew. Chem., Int. Ed. Engl.
1993,
32:
131 ; Angew. Chem. 1993 , 105 , 137
11c Tietze LF.
Chem. Rev.
1996,
96:
115
12a Barrett AGM.
Kamimura A.
J. Chem. Soc., Chem. Commun.
1995,
17:
1755
12b Tsukada N.
Nishimura TK.
Tsubouchi H.
Ono M.
Hayama T.
Nagaoka Y.
Tomioka K.
Tetrahedron Lett.
2003,
44:
2323
12c Tsukada N.
Shimida T.
Gyoung YS.
Asao N.
Yamamoto Y.
J. Org. Chem.
1995,
60:
143
13a Hara O.
Sugimoto K.
Makino K.
Hamada Y.
Synlett
2004,
1625
13b Rao HSP.
Senthilkumar SP.
J. Org. Chem.
2004,
69:
2591
13c Makino K.
Hara O.
Takiguchi Y.
Katano T.
Asakawa Y.
Hatano K.
Hamada Y.
Tetrahedron Lett.
2003,
44:
8925
13d Huang X.
Xiong Z.-C.
Chem. Commun.
2003,
14:
1714
13e Yamamoto Y.
Momiyama N.
Yamamoto H.
J. Am. Chem. Soc.
2004,
126:
5962
14a Paulsen H.
Antons S.
Brandes A.
Lögers M.
Müller SN.
Naab P.
Schmeck C.
Schneider S.
Stoltefuß J.
Angew. Chem. Int. Ed.
1999,
38:
3373 ; Angew. Chem. 1999 , 111 , 3574
14b Schneider C.
Reese O.
Angew. Chem. Int. Ed.
2000,
39:
2948 ; Angew. Chem. 2000 , 112 , 3074
14c Kamimura A.
Mitsudera H.
Omata Y.
Matsuura K.
Shirai M.
Kakehi A.
Tetrahedron
2002,
58:
9817
14d Huang X.
Xie MH.
Org. Lett.
2002,
4:
1331
14e Huang X.
Xie MH.
J. Org. Chem.
2002,
67:
8895
14f Arai T.
Sasai H.
Aoe K.-I.
Okamura K.
Date T.
Shibasaki M.
Angew. Chem., Int. Ed. Engl.
1996,
35:
104 ; Angew. Chem. 1996 , 108 , 103
14g Halland N.
Aburel PS.
Jørgensen KA.
Angew. Chem. Int. Ed.
2004,
43:
1272 ; Angew. Chem . 2004 , 116 , 1292
15a Satoh T.
Kitoh Y.
Onda K.-I.
Takana K.
Yamakawa K.
Tetrahedron
1994,
50:
4957
15b Evans DA.
Tedrow JS.
Shaw JT.
Downey CW.
J. Am. Chem. Soc.
2002,
124:
392
16a Thibonnet J.
Knochel P.
Tetrahedron Lett.
2000,
41:
3319
16b Thibonnet J.
Vu VA.
Berillon L.
Knochel P.
Tetrahedron
2002,
58:
4787
17 Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited as supplementary publication no. CCDC-268832 with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
18 Chandrasekhar S.
Narsihmulu C.
Reddy MR.
Reddy MS.
Tetrahedron Lett.
2003,
44:
2583
19 Sokolov V.V.
Es-Sayed M.
De Meijere A. unpublished results
