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Volumn 127, Issue 10, 1994, Pages 1959-1968

(R)‐1,2,2‐Triphenyl‐2‐(trimethylsiloxy)ethyl Propionate: anti‐Selective and Diastereofacially Selective Aldol Addition; Diastereoselective Silylation and Alkylation

(3) Sacha, Hubert a Waldmüller, Delia b Braun, Manfred a

a HEINRICH HEINE UNIVERSITY (Germany)

b BROWN UNIVERSITY (United States)

Author keywords

Aldol reaction; Chiral etiolate; Mandelic acid

Indexed keywords

EID: 0000151073 PISSN: 00092940 EISSN: 10990682 Source Type: Journal
DOI: 10.1002/cber.19941271020 Document Type: Article

Times cited : (22)

References (79)

1
- 84989417553
- Part of the Dissertation of, Universität Düsseldorf
- (1993)
- Sacha, H.¹

2
- 0001924336
- [2a]
- (1982) Top. Stereochem. , vol.13 , pp. 1-115
- Evans, D.A.¹ Nelson, J.V.² Taber, T.R.³

3
- 84989429675
- chapter 2
- 2b, J. D. Morrison, Academic Press, New York, part B
- (1984) Asymmetric Synthesis , vol.3
- Heathcock, C.H.¹

4
- 84985619546
- Doppelte Stereodifferenzierung und eine neue Strategie zur Stereokontrolle in der Organischen Synthese
- [c]
- (1985) Angewandte Chemie , vol.97 , pp. 1-31
- Masamune, S.¹ Choy, W.² Petersen, J.S.³ Sita, L.R.⁴

5
- 84985530075
- (1985) Angew. Chem. Int. Ed. Engl. , vol.24 , pp. 1-30

6
- 84973329202
- Stereoselektive Aldolreaktionen mit α-unsubstituierten chiralen Enolaten
- [d]
- (1987) Angewandte Chemie , vol.99 , pp. 24-37
- Braun, M.¹

7
- 0001829231
- (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 24-37

8
- 84989419013
- chapter 1.6
- 2e, B. M. Trost, Pergamon Press, Oxford
- (1993) Comprehensive Organic Syntheses , vol.2
- Heathcock, C.H.¹

9
- 84989429705
- chapter 1.7
- [f], B. M. Trost, Pergamon Press, Oxford
- (1993) Comprehensive Organic Syntheses , vol.2
- Moon Kim, B.¹ Williams, S.F.² Masamune, S.³

10
- 0001088334
- [g], V. Snieckus, JAI Press, Greenwich, CT, USA
- (1992) Advances in Carbanion Chemistry , vol.1 , pp. 177-247
- Braun, M.¹

11
- 0000967903
- Recent advances in Stereoselective Aldol Reactions of ester and thioester enolates
- 20b
- (1993) J. Prakt. Chem. , vol.335 , pp. 653-724
- Braun, M.¹ Sacha, H.²

12
- 0012016624
- [3a]
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127-2129
- Evans, D.A.¹ Bartroli, J.² Shih, T.L.³

13
- 0002049209
- [b]
- (1987) Tetrahedron Lett. , vol.28 , pp. 39-42
- Evans, D.A.¹ Sjogren, E.B.² Weber, A.E.³ Conn, R.E.⁴

14
- 0001272178
- 2a, h‐f and references given therein
- (1985) Tetrahedron Lett. , vol.26 , pp. 5807-5810
- Katsuki, T.¹ Yamaguchi, M.²

15
- 0012016415
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 1566-1568
- Masamune, S.¹ Choy, W.² Kerdesky, F.J.³ Imperiali, B.⁴

16
- 0000012047
- See also ref. [2e, f‐] and references given therein
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 5722-5728
- Siegel, C.¹ Thornton, E.R.²

17
- 0009529363
- Aldolkondensation mit hoher Stereoselektivität durch Verwendung eines enantioselektiven chiralen Enolats
- In this article, we will follow the syn, anti nomenclature proposed by Masamune. The carbon chain containing the two asymmetric centers is drawn in a zigzag fashion. In the syn isomers, both substituents of the stereogenic centers are directed either towards or away from the viewer. Cf.
- (1980) Angewandte Chemie , vol.92 , pp. 573-575
- Masamune, S.¹ Ali² Snitman, D.L.³ Garvey, D.S.⁴

18
- 84985553225
- (1980) Angew. Chem. Int. Ed. Engl. , vol.19 , pp. 557

19
- 0012078808
- (1984) Tetrahedron , vol.40 , pp. 2309-2315
- Meyers, A.I.¹ Yamamoto, Y.²

20
- 84989433492
- Chem. Lett.
- (1985) , pp. 1217-1220
- Narasaka, K.¹ Miwa, T.²

21
- 84985633277
- Enantio- undanti-diastereoselektive Aldoladditionen von Acetaten und Propionaten überO-Silylketenacetale
- (1985) Angewandte Chemie , vol.97 , pp. 874-876
- Helmchen, G.¹ Leikauf, U.² Taufer‐Knöpfel, I.³

22
- 84985633277
- (1985) Angew. Chem. Int. Ed. Eng. , vol.24 , pp. 874

23
- 84985538196
- Asymmetric and ?anti?-Selective Aldolisations of Acetates and Propionates. Preliminary Communication
- (1986) Helvetica Chimica Acta , vol.69 , pp. 1699-1703
- Oppolzer, W.¹ Marco‐Contelles, J.²

24
- 0024816607
- (1989) Tetrahedron Lett. , vol.30 , pp. 7121-7124
- Paterson, I.¹ Goodman, J.M.² Isaka, M.³

25
- 0000694191
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 9672-9674
- Myers, A.G.¹ Widdowson, K.L.²

26
- 0344137670
- (1991) J. Org. Chem. , vol.56 , pp. 2499-2506
- Van Draanen, N.A.¹ Arseniyadis, S.² Crimmins, M.T.³ Heathcock, C.H.⁴

27
- 0342713705
- (1991) J. Org. Chem. , vol.56 , pp. 5747-5750
- Walker, M.A.¹ Heathcock, C.H.²

28
- 0025968773
- (1991) Tetrahedron Lett. , vol.32 , pp. 61-64
- Oppolzer, W.¹ Starkemann, C.² Rodriguez, I.³ Bernardinelli, G.⁴

29
- 0026553351
- (1992) Tetrahedron , vol.48 , pp. 2127-2142
- Evans, D.A.¹ Ng, H.P.² Clark, J.S.³ Rieger, D.L.⁴

30
- 0000384618
- (1992) J. Org. Chem. , vol.57 , pp. 5173-5177
- Gennari, C.¹ Hewkin, C.T.² Molinari, F.³ Bernardi, A.⁴ Comotti, A.⁵ Goodman, J.M.⁶ Paterson, I.⁷

31
- 0026697882
- 14
- (1992) Tetrahedron , vol.48 , pp. 7979-8006
- Banks, M.R.¹ Blake, A.J.² Cadogan, J.I.G.³ Dawson, I.M.⁴ Gosney, I.⁵ Grant, K.J.⁶ Gaur, S.⁷ Hodgson, P.K.G.⁸ Knight, K.S.⁹ Smith, G.W.¹⁰ Stevenson, D.E.¹¹

32
- 0037545891
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 5250-5252
- Theopold, K.H.¹ Becker, P.N.² Bergman, R.G.³

33
- 0000274626
- (1985) Tetrahedron Lett. , vol.26 , pp. 2125-2128
- Davies, S.G.¹ Dordor‐Hedgecock, I.M.² Warner, P.³

34
- 0001353039
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 8279-8281
- Masamune, S.¹ Sato, T.² Kim, B.M.³ Wollmann, T.A.⁴

35
- 0013372519
- (1987) Tetrahedron Lett. , vol.28 , pp. 2841-2844
- Short, R.P.¹ Masamune, S.²

36
- 0025296017
- (1990) Tetrahedron Lett. , vol.31 , pp. 3863-3866
- Reetz, M.T.¹ Rivadeneira, E.² Niemeyer, C.³

37
- 0025906950
- (1991) Tetrahedron Lett. , vol.32 , pp. 2857-2860
- Corey, E.J.¹ Choi, S.²

38
- 0000407979
- (1991) J. Org. Chem. , vol.56 , pp. 2276-2278
- Kiyooka, S.¹ Kaneko, Y.² Komura, M.³ Matsuo, H.⁴ Nakano, M.⁵

39
- 0026525179
- (1992) Tetrahedron Lett. , vol.33 , pp. 1729-1732
- Parmee, E.R.¹ Hong, Y.² Tempkin, O.³ Masamune, S.⁴

40
- 0026706450
- (1992) Tetrahedron Lett. , vol.33 , pp. 4927-4930
- Kiyooka, S.¹ Kaneko, Y.² Kume, K.³

41
- 0000241934
- [8a]
- (1984) Tetrahedron Lett. , vol.25 , pp. 5031-5034
- Braun, M.¹ Devant, R.²

42
- 84907938122
- Stereoselektive Aldolreaktionen mit (R)- und (S)-(2-Hydroxy-1,2,2-triphenylethyl)acetat und verwandten Glycolmonoacetaten
- [b]
- (1988) Chemische Berichte , vol.121 , pp. 397-406
- Devant, R.¹ Mahler, U.² Braun, M.³

43
- 0001436310
- Reagent-controlled addition of (R)- and (S)-2-Hydroxy-1,2,2-triphenylethyl acetate to chiral aldehydes
- [c]
- (1988) Chemische Berichte , vol.121 , pp. 2035-2044
- Mahler, U.¹ Devant, R.M.² Braun, M.³

44
- 84989427610
- 2h.

45
- 0027068030
- Recent examples
- (1992) J. Org. Chem. , vol.57 , pp. 7143-7151
- Patel, D.V.¹ Schmidt, R.J.² Gordon, E.M.³

46
- 84989478909
- Liebigs Ann. Chem.
- (1993) , pp. 1091-1098
- Gräf, S.¹ Braun, M.²

47
- 84858065517
- Anti- und diastereofacial-selektive Aldolreaktionen mit (R)-(2-Siloxy-1,2,2-triphenylethyl)propionat
- Preliminary communication
- (1991) Angewandte Chemie , vol.103 , pp. 1369-1371
- Braun, M.¹ Sacha, H.²

48
- 33748231735
- (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1318-1320

49
- 0002976417
- (1993) Org. Synth. , vol.72 , pp. 32-36
- Braun, M.¹ Gräf, S.² Herzog, S.³

50
- 0000145196
- (1982) Org. React. N. Y. , vol.28 , pp. 203-331
- Mukaiyama, T.¹

51
- 0007223030
- (1993) Org. Synth. , vol.72 , pp. 38-47
- Braun, M.¹ Gräf, S.²

52
- 0000262287
- (1987) J. Org. Chem. , vol.52 , pp. 2754-2760
- Gennari, C.¹ Colombo, L.² Bertolini, G.³ Schimperna, G.⁴

53
- 84989435533
- 3 = Tris[3‐(2,2,3,4,4,4‐heptafluoro‐1‐hydroxybutylidene)‐d‐camphorato]‐euroeuropium (Aldrich).

54
- 84989455654
- Dissertation, Universität Würzburg
- (1986)
- Taufer‐Knöpfel, I.¹

55
- 0010640653
- (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
- Dale, J.A.¹ Dull, D.L.² Mosher, H.S.³

56
- 0001697761
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6339-6348
- Roush, W.R.¹ Ando, K.² Powers, D.B.³ Palkowitz, A.D.⁴ Halterman, R.L.⁵

57
- 0001153549
- (1991) J. Org. Chem. , vol.56 , pp. 2098-2106
- Yamago, S.¹ Machii, D.² Nakamura, E.³

58
- 0000731925
- 20, Tetrahedron Lett.
- (1975) , pp. 3975-3978
- Ireland, R.E.¹ Willard, A.K.²

59
- 0005927219
- 20b For a recent review, see:, R. Scheffold, Verlag Helvetica Chimica Acta — VCH, Basel — Weinheim, 1992, p.
- (1992) Modern Synthetic Methods , pp. 1-102
- Heathcock, C.H.¹

60
- 0027104310
- (1992) Tetrahedron Lett. , vol.33 , pp. 7885-7888
- Tanaka, F.¹ Fuji, K.²

61
- 0027054659
- (1992) Tetrahedron Lett. , vol.33 , pp. 8005-8006
- Munchhof, M.J.¹ Heathcock, C.H.²

62
- 0000931787
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2418-2419
- Larson, G.L.¹ Fuentes, L.M.²

63
- 0001554576
- The chemistry of .alpha.-silyl carbonyl compounds. 17. Methyldiphenylsilylation of ester and lactone enolates
- (1988) The Journal of Organic Chemistry , vol.53 , pp. 633-638
- Larson, G.L.¹ de Maldanado, V.C.² Fuentes, L.M.³ Torres, L.E.⁴

64
- 0001405474
- Enantioselektive Synthese von α-Trialkylsilylketonen und -aldehyden
- (1987) Angewandte Chemie , vol.99 , pp. 359-360
- Enders, D.¹ Bhushan Lohray, B.²

65
- 84985502386
- (1987) Angew. Chem. Int. Ed. Engl. , vol.26 , pp. 351

66
- 84943913171
- O-Silylation and Attempted O-Alkylation of Lithium Ester Enolates. The Synthesis of O-Silyl Ketene Acetals
- (1973) Synthetic Communications , vol.3 , pp. 67-72
- Rathke, M.W.¹ Sullivan, D.F.²

67
- 49649134694
- (1972) J. Organomet. Chem. , vol.46 , pp. 73-87
- Ainsworth, C.¹ Kuo, Y.²

68
- 0000545132
- Diastereo- und enantioselektive Aldolreaktionen via α-Silylketone, asymmetrische Synthese des Aggregationspheromons Sitophilur
- (1988) Angewandte Chemie , vol.100 , pp. 594-596
- Enders, D.¹ Bhushan Lohray, B.²

69
- 84990095595
- (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 581

70
- 84985727190
- Regio-, Diastereo-, and Enantioselective Synthesis ofvic-Diols via α-Silyl Ketones According to the SAMP/RAMP Hydrazone Method
- (1991) Chemische Berichte , vol.124 , pp. 219-226
- Enders, D.¹ Nakai, S.²

71
- 84989455985
- chapter 1
- For reviews on the diastereoselective alkylation of chiral enolates, see:, J. D. Morrison, Academic Press, New York, part 2
- (1984) Asymmetic Synthesis , vol.3
- Evans, D.A.¹

72
- 84989479979
- chapter 3
- J. D. Morrison, Academic Press, New York, part 2
- (1984) Asymmetic Synthesis , vol.3
- Lutomski, K.A.¹ Meyers, A.I.²

73
- 84989410951
- chapter 4
- J. D. Morrison, Academic Press, New York, part 2
- (1984) Asymmetic Synthesis , vol.3
- Enders, D.¹

74
- 0003598098
- R. Scheffold, Springer Verlag, Berlin
- (1986) Modern Synthetic Methods 1986 , pp. 125-259
- Seebach, D.¹ Imwinkelried, R.² Weber, T.³

75
- 84989448686
- chapter 1.1
- B. M. Trost, Pergamon Press, Oxford
- (1993) Comprehensive Organic Synthesis , vol.3
- Caine, D.¹

76
- 85007975161
- Stereochemical Studies. II. Thermal and Photochemical Decompositions of Optically Active Alkyl Azidoformates
- (1968) CHEMICAL & PHARMACEUTICAL BULLETIN , vol.16 , pp. 1953-1971
- Terashima, S.¹ Yamada, S.‐I.²

77
- 84989411452
- (Arizona Board of Regents), US Pat., 4,978,744, 18.12.
- (1990)
- Petitt, G.R.¹ Singh, S.B.²

78
- 84986937704
- (1991) Chem. Abstr. , vol.114 , pp. 164824 v

79
- 84989497240
- Futher details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich‐technische Information mbH, D‐76344 Eggenstein‐Leopoldshafen, on quoting the depository numbers CSD‐58413, the names of the authors, and the journal citation.

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