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1
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0004015228
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Trost, B. M, Ed, Pergamon Press: Oxford, U.K
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(a) Comprehensive Organic Syntheses; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2.
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(1991)
Comprehensive Organic Syntheses
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2
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0004015228
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Trost, B. M, Ed, Pergamon Press: Oxford, U.K
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(b) Comprehensive Organic Syntheses; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 1.
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(1991)
Comprehensive Organic Syntheses
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6
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0003913629
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Otera, J, Ed, Wiley-VCH: Weinheim, Germany, Chapter 10
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(a) Chemler, S. R.; Roush, W. R. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 10.
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(2000)
Modern Carbonyl Chemistry
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Chemler, S.R.1
Roush, W.R.2
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7
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0003913629
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Otera, J, Ed, Wiley-VCH: Weinheim, Germany, Chapter 11
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(b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 11.
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(2000)
Modern Carbonyl Chemistry
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Denmark, S.E.1
Almstead, N.G.2
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8
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0037073196
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For stereoselective additions to simple ketones, see: (a) Using tin-based reagents see: Yasuda, M.; Hirata, K.; Nishino, M.; Yamamoto, A.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13442 and see references cited therein,
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For stereoselective additions to simple ketones, see: (a) Using tin-based reagents see: Yasuda, M.; Hirata, K.; Nishino, M.; Yamamoto, A.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13442 and see references cited therein,
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9
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34247857460
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For a zinc version (allylic zincs were prepared from Zn (5 equiv), LiCl (1.2 equiv), and allyl halides (1 equiv)) see: Ren, H.; Dunet, G.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2007, 129, 5376.
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(b) For a zinc version (allylic zincs were prepared from Zn (5 equiv), LiCl (1.2 equiv), and allyl halides (1 equiv)) see: Ren, H.; Dunet, G.; Mayer, P.; Knochel, P. J. Am. Chem. Soc. 2007, 129, 5376.
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10
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0001441913
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In another Zn version, using a pre-prepared dry Zn, a mixture of both γ-adduct and α-adduct with a moderate to very good selectivity was observed for aldehydes and ketones, and the stereochemistry assignment of the γ-adducts was not established due to their decomposition. And only a pre-prepared Zn-Cu couple under acidic condition afforded the α-adducts, see: Rice, L. E, Boston, M. C, Finklea, H. O, Suder, B. J, Frazier, J. O, Hudlicky, T. J. Org. Chem. 1984, 49, 1845
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(c) In another Zn version, using a pre-prepared dry Zn, a mixture of both γ-adduct and α-adduct with a moderate to very good selectivity was observed for aldehydes and ketones, and the stereochemistry assignment of the γ-adducts was not established due to their decomposition. And only a pre-prepared Zn-Cu couple under acidic condition afforded the α-adducts, see: Rice, L. E.; Boston, M. C.; Finklea, H. O.; Suder, B. J.; Frazier, J. O.; Hudlicky, T. J. Org. Chem. 1984, 49, 1845.
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11
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37549041279
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A cinnamyl Grignard reagent with acetophenone gave a modest selectivity ds 70530, see ref 3a
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(d) A cinnamyl Grignard reagent with acetophenone gave a modest selectivity (ds 70530), see ref 3a.
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12
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33748428923
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(e) Tietze, L F.; Kinzel, T.; Schmatz, S. J. Am. Chem. Soc. 2006, 128, 11483.
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J. Am. Chem. Soc
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Tietze, L.F.1
Kinzel, T.2
Schmatz, S.3
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13
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3242808098
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(f) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
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J. Am. Chem. Soc
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Wada, R.1
Oisaki, K.2
Kanai, M.3
Shibasaki, M.4
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16
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0032334348
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(b) Yasuda, M.; Kitahara, N.; Fujibayashi, T.; Baba, A. Chem. Lett. 1998, 743.
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(1998)
Chem. Lett
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Yasuda, M.1
Kitahara, N.2
Fujibayashi, T.3
Baba, A.4
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17
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0000946629
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(c) Casolari, S.; D'Addario, D.; Tagliavini, E. Org. Lett. 1999, 1, 1061.
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(1999)
Org. Lett
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Casolari, S.1
D'Addario, D.2
Tagliavini, E.3
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18
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33845278851
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(a) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
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(1988)
J. Org. Chem
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Araki, S.1
Ito, H.2
Butsugan, Y.3
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22
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1042275565
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(e) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B. S. Tetrahedron 2004, 60, 1959.
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Tetrahedron
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Nair, V.1
Ros, S.2
Jayan, C.N.3
Pillai, B.S.4
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24
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0008593490
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Yamamoto, H, Ed, Wiley-VCH: Weinheim, Germany
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(g) Marshall, J. A. In Lewis Acids in Organic Synthesis; Yamamoto, H., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, p 453.
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Lewis Acids in Organic Synthesis
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Marshall, J.A.1
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29
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0000926764
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For some innovative reports on In-mediated diastereoselective allylations with unsubstituted allyl halides, see: (a) Lobben, P. C, Paquette, L. A. J. Org. Chem. 1998, 63, 6990
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For some innovative reports on In-mediated diastereoselective allylations with unsubstituted allyl halides, see: (a) Lobben, P. C.; Paquette, L. A. J. Org. Chem. 1998, 63, 6990.
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30
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(b) Paquette, L. A.; Bennett, G. D.; Isaac, M. B.; Chhatriwala, A. J. Org. Chem. 1998, 63, 1836.
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(1998)
J. Org. Chem
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Paquette, L.A.1
Bennett, G.D.2
Isaac, M.B.3
Chhatriwala, A.4
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35
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0028430856
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(c) Chan, T. H.; Li, C.-J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
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(1994)
Can. J. Chem
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Chan, T.H.1
Li, C.-J.2
Lee, M.C.3
Wei, Z.Y.4
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37
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(e) Miao, W.; Chung, L. W.; Wu, Y.-D.; Chan, T. H. J. Am. Chem. Soc. 2004, 126, 13326.
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(2004)
J. Am. Chem. Soc
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, pp. 13326
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Miao, W.1
Chung, L.W.2
Wu, Y.-D.3
Chan, T.H.4
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38
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0037433608
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(f) Tan, K.-T.; Chng, S.-S.; Cheng, H.-S.; Loh, T.-P. J. Am. Chem. Soc. 2003, 125, 2958.
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(2003)
J. Am. Chem. Soc
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Tan, K.-T.1
Chng, S.-S.2
Cheng, H.-S.3
Loh, T.-P.4
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39
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37549045585
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Isomers and their ratio could not be precisely determined
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(g) Isomers and their ratio could not be precisely determined.
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40
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28744445551
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For our aimed studies on the stereoselective metal-employed additions to ketones, see: a
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For our aimed studies on the stereoselective metal-employed additions to ketones, see: (a) Babu, S. A.; Yasuda, M.; Shibata, I.; Baba, A. J. Org. Chem. 2005, 70, 10408.
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(2005)
J. Org. Chem
, vol.70
, pp. 10408
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Babu, S.A.1
Yasuda, M.2
Shibata, I.3
Baba, A.4
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41
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33746603961
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and references cited therein
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(b) Babu, S. A.; Yasuda, M.; Okabe, Y.; Shibata, I.; Baba, A. Org. Lett. 2006, 8, 3029 and references cited therein.
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(2006)
Org. Lett
, vol.8
, pp. 3029
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Babu, S.A.1
Yasuda, M.2
Okabe, Y.3
Shibata, I.4
Baba, A.5
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0035924965
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(c) Yasuda, M.; Okamoto, K.; Sako, T.; Baba, A. Chem. Commun. 2001, 157.
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(2001)
Chem. Commun
, pp. 157
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Yasuda, M.1
Okamoto, K.2
Sako, T.3
Baba, A.4
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43
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10044234065
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(d) Babu, S. A.; Yasuda, M.; Shibata, I.; Baba, A. Org. Lett. 2004, 6, 4475.
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(2004)
Org. Lett
, vol.6
, pp. 4475
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Babu, S.A.1
Yasuda, M.2
Shibata, I.3
Baba, A.4
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44
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37549002854
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The stereochemistry of the product 3i was unambiguously established from X-ray analysis.
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(e) The stereochemistry of the product 3i was unambiguously established from X-ray analysis.
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45
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33645971287
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During our comprehensive investigations on the In-based stereoselective additions of the substituted allylic halides to simple ketones and alkoxy/hydroxy ketones, recently, a partial report with few examples limited to benzoin and cinnamyl bromide appeared; Kumar, S, Kaur, P, Mittal, A, Singh, P. Tetrahedron 2006, 62, 4018
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(f) During our comprehensive investigations on the In-based stereoselective additions of the substituted allylic halides to simple ketones and alkoxy/hydroxy ketones, recently, a partial report with few examples limited to benzoin and cinnamyl bromide appeared; Kumar, S.; Kaur, P.; Mittal, A.; Singh, P. Tetrahedron 2006, 62, 4018.
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46
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37549012126
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The stereochemistries of 6e (syn isomer) and 6g (syn-syn isomer, from benzoinmethyl ether 1i) were unambiguously determined from the X-ray structure analyses. For an analogue compound obtained from the reaction of benzoin and cinnamyl bromide E-geometry, a syn-anti stereochemistry was proposed, see ref 8f
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(g) The stereochemistries of 6e (syn isomer) and 6g (syn-syn isomer, from benzoinmethyl ether 1i) were unambiguously determined from the X-ray structure analyses. For an analogue compound obtained from the reaction of benzoin and cinnamyl bromide (E-geometry), a syn-anti stereochemistry was proposed, see ref 8f.
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48
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0000266551
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(b) Sato, K.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 6429.
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(1989)
J. Am. Chem. Soc
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, pp. 6429
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Sato, K.1
Kira, M.2
Sakurai, H.3
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49
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37549003604
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1H NMR spectral region,
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1H NMR spectral region,
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50
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37549032691
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In the case of cinnamyl bromide with In also a facile formation of two species in THF-d8-D2O was observed, which indicated that the γ-substituted allyl In species are also stable in aqueous condition. They would be RIn(I) and RIn(III)-type species as already discussed in refs 7d and 8a-c. Based on the observed astonishing diastereoselectivities and strong chelation as the key point; plausibly, a low-valent RIn(I)-type transient species could be projected as very reactive intermediate, see SI
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2O was observed, which indicated that the γ-substituted allyl In species are also stable in aqueous condition. They would be RIn(I) and RIn(III)-type species as already discussed in refs 7d and 8a-c. Based on the observed astonishing diastereoselectivities and strong chelation as the key point; plausibly, a low-valent RIn(I)-type transient species could be projected as very reactive intermediate, see SI.
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51
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37549050505
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As noted in ref 3c about the instability of products in column purification, in our case, the homoallyl alcohols 7g-j/6a-g were stable even after several months. But the products 7a-f were slowly decomposed after several months. We unambiguously assigned the stereochemistry of the γ-adducts 6a-g/7g-j, see SI
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(c) As noted in ref 3c about the instability of products in column purification, in our case, the homoallyl alcohols 7g-j/6a-g were stable even after several months. But the products 7a-f were slowly decomposed after several months. We unambiguously assigned the stereochemistry of the γ-adducts 6a-g/7g-j, see SI.
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