Abstract
Enantiomerically pure phenols are readily available in a straightforward sequence starting from (+)-dehydroabietylamine. Detailed synthetic protocols, analytical data and conversion to a monodentate phosphite ligand are presented.
Key words
phenols - chiral pool - amines - natural products - dehydroabietane
References
1a 1 ), see: Campbell WP.
Todd D.
J. Am. Chem. Soc.
1942,
64:
928
1b 2 ), and (+)-totarol (3 ), see: Cambie RC.
Cox RE.
Croft KD.
Sidwell D.
Phytochemistry
1983,
22:
1163
2a Nagata H.
Miyazawa N.
Ogasawara K.
Org. Lett.
2001,
3:
1737
2b Hao X.-J.
Node M.
Fuji K.
J. Chem. Soc., Perkin Trans. 1
1992,
1505
2c Marcos IS.
Cubillo MA.
Moro RF.
Diez D.
Basabe P.
Sanz F.
Urones JG.
Tetrahedron Lett.
2003,
44:
8831
3 Boyle PH.
Quart. Rev.
1971,
25:
323
4 Commercially available (+)-dehydroabietylamine contains about 60% of 4 contaminated with the remainings of other amines and hydrocarbons.
5 All procedures were reproduced in scales of up to 25 g.
6 Rufer C.
Albrecht R.
Schroeder E.
Liebigs Ann. Chem.
1969,
728:
193
7 Czekelius C.
Carreira EM.
Angew. Chem. Int. Ed.
2005,
44:
612 ; Angew. Chem. 2005 , 117 , 618
8 Koch SSC.
Chamberlin R.
Synth. Commun.
1989,
19:
829
9 Zemplén G.
Kunz A.
Ber. Dtsch. Chem. Ges.
1923,
56:
1705
10 Gilbert KE.
Borden WT.
J. Org. Chem.
1979,
44:
659
11 Transition Metals for Organic Synthesis
2nd ed.:
Beller M.
Bolm C.
Wiley-VCH;
Weinheim:
2004.
12a Reetz MT.
Meiswinkel A.
Mehler G.
Angermund K.
Graf M.
Thiel W.
Mynott R.
Blackmond DG.
J. Am. Chem. Soc.
2005,
127:
10305
12b Reetz MT.
Fu Y.
Meiswinkel A.
Angew. Chem. Int. Ed.
2006,
45:
1412 ; Angew. Chem. 2006 , 118 , 1440
12c Van den Berg M.
Minnaard AJ.
Schudde EP.
van Esch J.
de Vries AHM.
de Vries JG.
Feringa BL.
J. Am. Chem. Soc.
2000,
122:
11539
13a Jensen JF.
Svendsen BY.
La Cour TV.
Pedersen HL.
Johannsen M.
J. Am. Chem. Soc.
2002,
124:
4558
13b Imbos R.
Minnaard AJ.
Feringa BL.
J. Am. Chem. Soc.
2002,
124:
184
13c Alexakis A.
Benhaim C.
Rosset S.
Humam M.
J. Am. Chem. Soc.
2002,
124:
5262
14 Nitro compound 12 is not inert towards phosphite derivatives and was therefore not used as precursor for phosphite ligands.
15 Yield corresponds to the content of (+)-dehydroabietylamine in the starting material, which was checked by GC methods.
16 CCDC 624454 and 624455 contain the supplementary crystallographic data for compounds 6 and 9 , respectively, of this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.
17 COLLECT
Nonius B.V.;
Delft:
1998.
18 Otwinowski Z.
Minor W.
Processing of X-ray Diffraction Data Collected in Oscillation Mode, In Methods in Enzymology, Macromolecular Crystallography, Part A
Vol. 276:
Carter CW.
Sweet RM.
Academic Press;
New York:
1997.
p.307-326
19a Blessing RH.
Acta Crystallogr., Sect. A
1995,
51:
33
19b Blessing RH.
J. Appl. Crystallogr.
1997,
30:
421
20 Otwinowski Z.
Borek D.
Majewski W.
Minor W.
Acta Crystallogr., Sect. A
2003,
59:
228
21 Sheldrick GM.
Acta Crystallogr. Sect. A
1990,
46:
467
22 Sheldrick GM.
Structure Refinement SHELXL-97
University of Göttingen;
Göttingen:
1997.
23 Van der Vlugt JI.
Hewat AC.
Neto S.
Sablong RM.
Mills AM.
Lutz M.
Spek AL.
Müller C.
Vogt D.
Adv. Synth. Catal.
2004,
346:
993
