-
2
-
-
34249991880
-
-
Lopez, P.; Siegmund, A.; Frohn, M.; Liu, L. Rishton, G. unpublished results.
-
-
-
-
3
-
-
34250018974
-
-
Frohn, M. J.; Hong, F.-T.; Liu, L.; Lopez, P.; Siegmund, A. C.; Tadesse, S.; Tamayo, N. WO 070932A2, 2005, Amgen Inc.
-
-
-
-
4
-
-
34250005595
-
-
note
-
® (renal failure).
-
-
-
-
5
-
-
34250007272
-
-
note
-
Compounds 1 and 2 contain two stereogenic centers, whereas 3 contains one homobenzylic amine stereocenter and a benzylic quaternary center.
-
-
-
-
7
-
-
34250007816
-
-
note
-
Facile cleavage and recycling are the main advantages of this chiral auxiliary over the standard Evans' oxazolidinone system.
-
-
-
-
9
-
-
34250029136
-
-
note
-
Average of multiple runs.
-
-
-
-
11
-
-
34250025530
-
-
note
-
80% of 9 isolated by crystallization. Additional 11% of 9 could be recovered from the mother liquors by column chromatography (91% yield total).
-
-
-
-
12
-
-
34249995874
-
-
note
-
Caution: Hydrazoic acid is a volatile and potentially explosive compound in a gaseous state. Handle with care. Avoid contact with heavy metal salts and alloys.
-
-
-
-
13
-
-
34250010738
-
-
note
-
First crop. Additional material could be recovered by chromatography of the mother liquors.
-
-
-
-
16
-
-
0037958740
-
-
Masumoto S., Usuda H., Suzuki M., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 5634-5635
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 5634-5635
-
-
Masumoto, S.1
Usuda, H.2
Suzuki, M.3
Kanai, M.4
Shibasaki, M.5
-
17
-
-
34249988092
-
-
note
-
O-Diphenylphosphinyl oxime. Unstable O-phosphinyl oximes (cf. Lopez, L.; Barrans, J. J. Chem. Soc., Perkin Trans. 1 1977, 1806-1811) rearrange thermally to N-phosphinyl imines via the radical mechanism (cf. Brown, C.; Hudson, R. F.; Maron, A.; Record, K. A. F. J. Chem. Soc., Chem. Commun. 1976, 663-664).
-
-
-
-
18
-
-
34249991056
-
-
note
-
Typical reaction time reported in Ref. 13 was 72 h at room temperature.
-
-
-
-
19
-
-
34250002406
-
-
note
-
The stereochemistry of the major product was not assigned. However, the stereochemistry shown in Scheme 4 follows the direction of the induction from Ref. 13.
-
-
-
-
22
-
-
34250017574
-
-
note
-
3 to mitigate these issues was not investigated.
-
-
-
-
25
-
-
1542375289
-
-
For recent reviews on aziridine chemistry, see:
-
For recent reviews on aziridine chemistry, see:. Hu X.E. Tetrahedron 60 (2004) 2701-2743
-
(2004)
Tetrahedron
, vol.60
, pp. 2701-2743
-
-
Hu, X.E.1
-
30
-
-
0030012954
-
-
Baldwin J.E., Farthing C.N., Rusell A.T., Schofield C.J., and Spivey A.C. Tetrahedron Lett. 37 (1996) 3761-3764
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 3761-3764
-
-
Baldwin, J.E.1
Farthing, C.N.2
Rusell, A.T.3
Schofield, C.J.4
Spivey, A.C.5
-
31
-
-
33750506733
-
-
Aziridines are preferentially ring-opened by soft, heteroatom-based nucleophiles (Ref. 21). For the most recent examples, see:
-
Aziridines are preferentially ring-opened by soft, heteroatom-based nucleophiles (Ref. 21). For the most recent examples, see:. Wu J., Sun X., and Sun W. Org. Biomol. Chem. 4 (2006) 4231-4235
-
(2006)
Org. Biomol. Chem.
, vol.4
, pp. 4231-4235
-
-
Wu, J.1
Sun, X.2
Sun, W.3
-
39
-
-
4143102531
-
-
For the earlier examples, see: Ref. 21
-
Ding C.-H., Dai L.-X., and Hou X.-L. Synlett (2004) 1691-1694 For the earlier examples, see: Ref. 21
-
(2004)
Synlett
, pp. 1691-1694
-
-
Ding, C.-H.1
Dai, L.-X.2
Hou, X.-L.3
-
40
-
-
34249997960
-
-
note
-
22d (3.5-10.1 equiv), Osowska-Pacewicka, K.; Zwierzak, A. Synthesis 1996, 333-335 (2-3 equiv). These methods are economically viable only if a carbon nucleophile is inexpensive and readily available.
-
-
-
-
41
-
-
34249999902
-
-
note
-
27a).
-
-
-
-
45
-
-
34250003336
-
-
note
-
Solubilization of copper salts effected by anhydrous lithium salts (LiCl or LiBr) also led to inactive copper species.
-
-
-
-
46
-
-
34249983304
-
-
note
-
Compounds (S,S)-12 and (S,R)-12 are orthogonally protected diamines 1 and 2, respectively.
-
-
-
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