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Volumn 25, Issue 36, 1984, Pages 3927-3930

Observations on the choice of Lewis acid and mode of addition for the Lewis acid mediated reaction of crotyltri-n-butylstannane with aldehydes: convenient and highly selective access to both erythro and threo products

(4) Keck, Gary E a Abbott, Duain E a Boden, Eugene P a Enholm, Eric J a

a UNIVERSITY OF UTAH (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000725791 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(84)80032-5 Document Type: Article

Times cited : (134)

References (17)

1
- 33847085986
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7107
- Yamamoto¹ Yatagai² Naruta³ Maruyama⁴

2
- 67650317827
- On the stereochemistry of allylmetal-aldehyde condensations. Preliminary communication
- More recently, synclinal transition state geometries have been suggested for similar reactions:, Note also reference 8
- (1983) Helvetica Chimica Acta , vol.66 , pp. 1655
- Denmark¹ Weber²

3
- 84918384972
- Parallel results have been observed for the analogous silanes. Note

4
- 0001057466
- (1984) Tetrahedron Lett. , vol.25 , pp. 265
- Keck¹ Boden²

5
- 0000705591
- (1984) Tetrahedron Lett. , vol.25 , pp. 1879
- Keck¹ Boden²

6
- 84918384886
- This experiment was performed using a 43.4:56.6 mixture of cis and trans crotyltri-n-butylstannane.

7
- 84918384885
- This experiment was performed using a 65.3:35.7 mixture of cis and trans crotyltri-n-butylstannane.

8
- 84918384884
- This experiment was performed using “normal” addition--i.e. addition of crotyltri-n-butylstannane to a solution containing Lewis acid and aldehyde.

9
- 84918384883
- This experiment was performed using “inverse” addition--i.e. addition of aldehyde to a solution prepared from Lewis acid and crotyltri-n-butylstannane.

10
- 0000234052
- Parallel results have been observed for the analogous silanes. Note
- (1983) Tetrahedron Lett. , vol.24 , pp. 2865
- Hayashi¹ Kabeta² Hamachi³ Komada⁴

11
- 0000751968
- Note, and references therein
- (1984) Tetrahedron Lett. , vol.25 , pp. 1883
- Keck¹ Abbott²

12
- 84918384882
- Product ratios expressed in this way should not be regarded as “hard” numbers for ratios greater than ∼20:1 since such ratios increase rapidly with very small changes in measured amounts of products. For example, a 95.24/4.76 distribution corresponds to 20:1 selectivity, while a 97.56/2.44 distribution corresponds to 40:1 selectivity.

13
- 84918384881
- 2O-hexane).

14
- 0001797499
- 3 via an internal delivery of the crotyl unit with a chairlike transition state. For a recent review of organotitanium compounds in organic synthesis, note
- (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 31
- Weidmann¹ Seebach²

15
- 0020173674
- Diastereogenic Addition of Crotylmetal Compounds to Aldehydes
- For reviews, note:
- (1982) Angewandte Chemie International Edition in English , vol.21 , pp. 555
- Hoffman¹

16
- 0000344737
- Oraganometallic Compounds for Stereoregulated Synthesis of Acyclic Systems. Their Application to the Synthesis of the Prelog-Djerassi Lactonic Acid
- 3 via an internal delivery of the crotyl unit with a chairlike transition state. For a recent review of organotitanium compounds in organic synthesis, comment
- (1982) HETEROCYCLES , vol.18 , pp. 357
- Yamamoto¹ Maruyama²

17
- 84918384880
- Support of this research by the Alfred P. Sloan Foundation and the National Institutes of Health (through grant GM-28961) is gratefully acknowledged.

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