Abstract
The lithium aldol reaction of α-chloroaldehydes provides 1,2-anti -configured β-ketochlorohydrins.
The scope of this reaction is demonstrated as well as its application
to the synthesis of the C4-C15 segment of haterumalide
NA.
Key words
α-chloroaldehydes - aldol reaction - stereoselective
synthesis - heterocycles - natural products
References
1a Erkkil A.
Majander I.
Pihko PM.
Chem. Rev.
2007,
107:
5416
1b MacMillan DWC.
Nature
2008,
455:
304
2 Worgull D.
Dickmeiss G.
Jensen KL.
Franke PT.
Holub N.
Jørgensen KA.
Chem.
Eur. J.
2011,
17: in press; DOI : 10.1002/chem.201100233
3 Núñez MG.
García P.
Moro RF.
Díez D.
Tetrahedron
2010,
66:
2089
4 Juhl K.
Jørgensen KA.
Angew. Chem. Int. Ed.
2003,
42:
1498
5a Kang B.
Mowat J.
Pinter T.
Britton R.
Org. Lett.
2009,
11:
1717
5b Kang B.
Chang S.
Decker S.
Britton R.
Org. Lett.
2010,
12:
1716
5c Draper J.
Britton R.
Org. Lett.
2010,
12:
4034
6a Brochu MP.
Brown SP.
MacMillan DWC.
J. Am. Chem.
Soc.
2004,
126:
4108
6b Amatore M.
Beeson TD.
Brown SP.
MacMillan DWC.
Angew.
Chem. Int. Ed.
2009,
48:
5121
7 Halland N.
Braunton A.
Bachmann S.
Marigo M.
Jørgensen KA.
J. Am. Chem. Soc.
2004,
126:
4790
8a Dekeukeleire S.
D’hooghe M.
Trnroos KW.
De Kimpe N.
J.
Org. Chem.
2010,
75:
5934
8b D’hooghe M.
Van Brabandt W.
Dekeukeleire S.
Dejaegher Y.
De Kimpe N.
Chem. Eur. J.
2008,
14:
6336
9a Takeda A.
Tsuboi S.
Wada S.
Kato H.
Bull. Chem. Soc. Jpn.
1972,
45:
1217
9b Pri-Bar I.
Pearlman PS.
Stille JK.
J. Org. Chem.
1983,
48:
4629
9c Barluenga J.
Alvarez F.
Concellón JM.
Yus M.
Synthesis
1986,
654
9d Barluenga J.
Alvarez F.
Concellón JM.
Bernad P.
Yus M.
Synthesis
1987,
318
9e Barbas CF.
Wang Y.-F.
Wong C.-H.
J.
Am. Chem. Soc.
1990,
112:
2013
9f Maruoka K.
Concepcion AB.
Murase N.
Oishi M.
Hirayama N.
Yamamoto H.
J. Am. Chem. Soc.
1993,
115:
3943
10 Borg T.
Danielsson J.
Somfai P.
Chem. Commun.
2010,
46:
1281
11 Takeda M.
Sato H.
Suenaga K.
Arimoto H.
Yamada K.
Ueda K.
Uemura D.
Tetrahedron Lett.
1999,
40:
6309
12 Teruya T.
Suenaga K.
Maruyama S.
Kurotaki M.
Kigoshi H.
Tetrahedron
2005,
61:
6561
13 Cee VJ.
Cramer CJ.
Evans DA.
J. Am. Chem. Soc.
2006,
128:
2920 ; and references cited therein
14 Kang B.
Britton R.
Org. Lett.
2007,
9:
5083
15 The stereochemical assignment of all
new β-ketochloro-hydrins was confirmed by conversion into
known compounds, or the corresponding epoxy alcohols (1. catecholborane,
THF, -10 ˚C; 2. KOH, EtOH, 0 ˚C
to r.t.) and subsequent analysis of coupling constants and NOE data.
16 Wheeler SE.
Moran A.
Pieniazek SN.
Houk KN.
J.
Phys. Chem. A
2009,
113:
10376
17 Evans DA.
Cee VJ.
Siska SJ.
J.
Am. Chem. Soc.
2006,
128:
9433
18 The β-ketochlorohydrins 13 , 18 , 20 , and 22 derived
from
19 Stadler M.
Anke H.
Stener O.
Tetrahedron
1994,
50:
12649
20 Kigoshi H.
Hayakawa I.
Chem. Rec.
2007,
7:
254
21a Kigoshi H.
Kita M.
Ogawa S.
Itoh M.
Uemura D.
Org.
Lett.
2003,
5:
957
21b Gu Y.
Snider BB.
Org. Lett.
2003,
5:
4385
21c Hoye T.
Wang J.
J. Am. Chem. Soc.
2005,
127:
6950
21d Schomaker JM.
Borhan B.
J. Am. Chem.
Soc.
2008,
130:
12228
21e Hayakawa I.
Ueda M.
Yamaura M.
Ikeda Y.
Suzuki Y.
Yoshizato K.
Kigoshi H.
Org. Lett.
2008,
10:
1859
21f Roulland E.
Angew. Chem.
Int. Ed.
2008,
47:
3762
21g Ueda M.
Yamaura M.
Ikeda Y.
Suzuki Y.
Yoshizato K.
Hayakawa I.
Kigoshi H.
J.
Org. Chem.
2009,
74:
3370
22 Kaneda K.
Uchiyama T.
Fujiwara Y.
Imanaka T.
Teranishi S.
J.
Org. Chem.
1979,
44:
55
23 Braese S.
Wertal H.
Frank D.
Vidovic D.
de Meijere A.
Eur.
J. Org. Chem.
2005,
4167
24 32 was
prepared in two steps from but-3-en-1-ol following the procedure
described in: Ghosh AK.
Jianfeng L.
Org. Lett.
2009,
11:
4164
25 For the preparation of α-chloroaldehydes
used in this work, see references 5, 6, 7, and 14.
