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Journal Name
Organic & Biomolecular Chemistry
DOI: 10.1039/C5OB01097G
Nakatsuji, J. Morita, T. Misaki and Y. Tanabe, Adv. Synth. Catal. 2006,
348, 2057.
†
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/c000000x
9.
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2015, 137, 999: A recent related enol tosylation method using
Ts2O−bases and successive SuzukiꢀMiyaura stereoretentive crossꢀ
coupling for the synthesis of chiral αꢀamino acid precursors.
1.
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10. 50 gꢀscale preparation of 1a was performed by the self TiꢀClaisen
condensation using methyl hexanoate with TiCl4 and Et3N at 0ꢀ5 ◦C
for 1 h (93% yield). See ESI. cf. a) R. Hamasaki, S. Funakoshi, T.
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11. For (Z)ꢀ2a; Use of TsCl−NMI−Et3N (or TMEDA) instead, resulted in
only 15ꢀ25% yield with the side formation of αꢀchlorinated byꢀproduct
of 1a. For (E)ꢀ2a; Uses of TsCl−NMI−LiOH (or TMEDA) instead,
gave only 20ꢀ30% yield.
12. (PhO)2POCl is commercially available in an industrial scale
exemplified by the synthsis of 1ꢀβꢀmethylcarbapenem. (a) A. H. Berks,
Tetrahedron 1996, 52. 331. (b) J. M. Williams, K. M. J. Brands, R. T.
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13. For example, Rf values of (E)ꢀ2j: 0.48, (Z)ꢀ2j: 0.45 (Hexane/EtOAc =
1:1).
3.
4.
14. The result resembles the case of the TsClꢀNMI intermediate.8a
15. (a) Pd(PPh3)4; (E): 10%, (Z): 13%. (b) Pd(PPh3)2Cl2; (E): 24%, (Z):
11%. (c) Pd(dppe)Cl2; (E): 25%, (Z): 0%. (d) Pd(dppf)Cl2; (E): 8%,
(Z): 0%. (e) Pd(OAc)2‒PCy3; (E): 12%, (Z): 0%. For details, see ESI.
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condensation between methyl phenylacetate and benzoyl chloride
using with TiCl4‒Et3N‒NMI at ‒45 ◦C for 1 h (74% yield). Ref. 8b.
See ESI.
18. Recent representative syntheses of (Z)ꢀtamoxifen. (a) K. Matsumoto
and M. Shindo, Adv. Synth. Catal. 2012, 354, 642. (b) G. Cahiez, A.
Moyeux and M. Poizat, Chem. Commun. 2014, 50, 8982. (c) K.
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Other previous syntheses cited therein.
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Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
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