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85030804812
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note
-
2Si: 349.2311. Found: 349.2297
-
-
-
-
22
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0036201102
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-
A.E. Jensen, W. Dohle, I. Sapountzis, D.M. Lindsey, A.V. Viet, and P. Knochel Synthesis 2002 565 569
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Synthesis
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Jensen, A.E.1
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24
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2142807290
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R.K. Dieter, G. Oba, C.M. Chandupatla, K.L. Topping, and R.T. Watson J. Org. Chem. 69 2004 3076 3086
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(2004)
J. Org. Chem.
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Dieter, R.K.1
Oba, G.2
Chandupatla, C.M.3
Topping, K.L.4
Watson, R.T.5
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28
-
-
85030805245
-
-
note
-
2: 316.2151. Found: 316.2161
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-
-
-
29
-
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0001692739
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-
2:281.2229.Found:281.2231. ToobtainfurtherproofoftherelativestereochemistrytheBocgroupwasremovedto liberatethesecondaryamine,nowamenableforasymmetricfunctionalisation. AttemptstoacylatetheresultingaminewithMosher'sacidchloridegroupfailedand gaveseveralsideproducts.Mostprobably,duetosterichindrancecausedbythe2, 6-allylgroups,sidereactionsatthe4-amineoccurred.(See:
-
2: 281.2229. Found: 281.2231. To obtain further proof of the relative stereochemistry the Boc group was removed to liberate the secondary amine, now amenable for asymmetric functionalisation. Attempts to acylate the resulting amine with Mosher's acid chloride group failed and gave several side products. Most probably, due to steric hindrance caused by the 2,6-allyl groups, side reactions at the 4-amine occurred. (See: T.R. Hoye, and M.K. Renner J. Org. Chem. 61 1996 2056 2064). Addition of Pirkle's amine (up to 1.5 equiv) only gave a shift of the peaks. The observation that no doubling of the peaks occurred points at an achiral compound thus supporting the previous coupling constant based 2,6-cis stereochemistry assignment
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J. Org. Chem.
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Hoye, T.R.1
Renner, M.K.2
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